1-phenylpyrrolidine-2-one-3-carboxamides

ABSTRACT

The invention relates to 1-phenylpyrrolidin-2-one-3-carboxamides of the formula I  
                 
 
where the variables R 1 , R 2 , R 3 , X, Y, A, n, R a , R b , R c , R d  and R e  are as defined in claim 1 and to their agriculturally useful salts. 
Moreover, the invention relates to the use of compounds I and/or their salts as herbicides; crop protection compositions comprising at least one 1-phenylpyrrolidin-2-one-3-carboxamide of the formula I and/or at least one agriculturally useful salt of I as active substances; and also a method for controlling unwanted vegetation, which comprises allowing a herbicidally effective amount of at least one 1-phenylpyrrolidin-2-one-3-carboxamide of the formula I or an agriculturally useful salt of I to act on plants, their habitat or on seed.

The present invention relates to 1-phenylpyrrolidin-2-one-3-carboxamides and their agriculturally useful salts, to compositions comprising such compounds and to the use of the 1-phenylpyrrolidin-2-one-3-carboxamides, of their salts or of compositions comprising them as herbicides.

WO 95/33719 describes 1-arylthiazolidinones, 1-aryloxazolidinones and 1-arylpyrrolidinones of the formula:

where A is an aromatic or heteroaromatic radical, n is 0 or 1, x is in particular S, O or CH₂, Y is in particular S, O, CH₂ or CH(CH₃) or a group NR⁶, Z is in particular NH or O, R¹ is preferably selected from unsubstituted or substituted alkyl, alkenyl, alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted phenyl, benzyl or hetaryl, acyl, alkoxycarbonylalkyl and silyl, R² and R³ are in particular hydrogen and R⁶ is inter alia hydrogen, formyl, unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl or unsubstituted or substituted aryl.

WO 95/33718 describes 1-phenylpyrrolidinethiones having herbicidal activity which, in the 3-position of the pyrrolidinethione ring, contain a group O—C(O)—NR¹R² where R¹R² are, for example, hydrogen, an unsubstituted or substituted hydrocarbon radical or hetaryl, or together with the nitrogen atom to which they are attached form a heterocycle.

Furthermore, U.S. Pat. No. 4,874,422 discloses herbicidally active 1-phenylpyrrolidin-2-one-3-carboxamides of the formula A

where X is hydrogen or halogen, Y and Z independently of one another are O or S, n is 0 or 1, R¹ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, phenyl, halophenyl, benzyl, halobenzyl, or alkyl which is substituted by alkoxy, alkylthio, phenyl, hydroxyl or cyano, R² is hydrogen or alkyl, R³ is alkyl or alkenyl and R⁴ is selected from the group consisting of hydrogen, halogen, methyl, trifluoromethyl, 1,1,2,2-tetrafluoroethyl, 1,1,2,2-tetrafluoroethyloxy, difluoromethoxy, trifluoromethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxyiminomethyl, methoxyimino-1-ethyl, benzyloxyiminomethyl and benzyloxyimino-1-ethyl.

The herbicidal activity of the 1-arylpyrrolidinones described in the prior art is not always satisfactory. Their selectivity for harmful plants is unsatisfactory, too. In particular, even at low application rates, such herbicides tend to interfere with the generation of chlorophyll even in crop plants, which is undesirable in principle and may lead to yield losses.

It is an object of the present invention to provide novel herbicidally active compounds which allow a better targeted control of unwanted plants than the known herbicides. Advantageously, the novel herbicides should be highly active against harmful plants. Moreover, high compatibility with crop plants is desirable. Moreover, the compounds should have no adverse effect on the chlorophyll synthesis in crop plants.

We have found that this object is achieved by 1-phenylpyrrolidin-2-one-3-carboxamides of the formula I defined below and their agriculturally useful salts:

where the variables R¹, R², R³, X, Y, A, n, R^(a), R^(b), R^(c), R^(d) and R^(e) are as defined below:

-   R¹ is hydrogen, OH, Cl, Br, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,     C₃-C₆-alkenyl, C₃-C₆-alkynyl, C(O)R⁴ or OC(O)R⁴; -   R² and R³ independently of one another are hydrogen, C₁-C₁₀-alkyl,     C₃-C₁₀-cycloalkyl, C₇-C₁₀-polycycloalkyl, C₃-C₈-alkenyl,     C₃-C₁₀-alkynyl, C₅-C₁₀-cycloalkenyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,     phenyl or 3- to 7-membered heterocyclyl, where the 9 last-mentioned     groups may be unsubstituted, partially or fully halogenated and/or     contain 1, 2 or 3 radicals selected from the group consisting of OH,     CN, NO₂, COOH, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,     C₁-C₄-haloalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkylthio,     C₁-C₄-haloalkyl-thio, unsubstituted or substituted phenyl, COOR⁵,     NR⁶R⁷, C(O)NR⁸SO₂R¹³, C(O)NR⁸R⁹ and 3- to 7-membered heterocyclyl,     and each heterocyclyl may contain 1, 2 or 3 heteroatoms selected     from the group consisting of oxygen, nitrogen, sulfur, a group NR¹⁰     and a group SO₂, and, if appropriate, 1, 2 or 3 carbonyl groups     and/or thiocarbonyl groups as ring members; and/or may contain a     ring-fused phenyl ring which is unsubstituted or substituted; or     -   R² and R³ with the group N-(A)_(n) to which they are attached         form a saturated 3- to 7-membered heterocycle which, in addition         to the nitrogen atom, may contain 1, 2 or a further 3         heteroatoms selected from the group consisting of oxygen,         nitrogen, sulfur and a group NR¹⁰ and, if appropriate, 1, 2 or 3         carbonyl groups and/or thiocarbonyl groups as ring members; -   R^(a), R^(b), R^(c), R^(d) and R^(e) independently of one another     are hydrogen, OH, CN, NO₂, halogen, C₁-C₁₀-alkyl, C₃-C₆-cycloalkyl,     C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl,     C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkylthio,     C₁-C₄-haloalkylthio, C(O)R⁴, COOR⁵, NR⁶R⁷, C(O)NR⁸R⁹, S(O)₂NR⁸R⁹,     S(O)R¹¹, S(O)₂R¹¹ or C₁-C₄-alkoxy-C₁-C₆-alkyl; or     -   two adjacent radicals R^(a) to R^(e) together with the atoms to         which they are attached form a 5-, 6- or 7-membered saturated or         unsaturated ring which may contain one or two heteroatoms         selected from the group consisting of nitrogen, oxygen, sulfur         and a group NR¹⁰ as ring-forming atom and/or may carry one, two,         three or four radicals selected from the group consisting of         halogen and C₁-C₄-alkyl; -   X, Y independently of one another are oxygen or sulfur; -   n is 0 or 1; -   A is O, S(O)_(k) or NR¹², where k is 0, 1 or 2; -   R⁴, R⁸, R⁹ independently of one another are hydrogen or C₁-C₄-alkyl; -   R⁵, R¹¹ are C₁-C₄-alkyl; -   R⁶, R⁷ independently of one another are hydrogen, C₁-C₆-alkyl,     C₃-C₆-alkenyl, C₃-C₆-alkynyl, C(O)R⁴, COOR⁵ or S(O)₂R¹¹; -   R¹⁰, R¹² independently of one another are hydrogen, C₁-C₆-alkyl,     C₃-C₆-alkenyl or C₃-C₆-alkynyl; and -   R¹³ is phenyl which is unsubstituted or carries 1, 2, 3 or 4     substituents, where the substituents are selected from the group     consisting of halogen, nitro, cyano, OH, alkyl, alkoxy, haloalkyl,     haloalkoxy, COOR⁵, NR⁶R⁷ and C(O)NR⁸R⁹.

Accordingly, the present invention relates to 1-phenyl-pyrrolidin-2-one-3-carboxamides of the formula I and their agriculturally useful salts.

Moreover, the present invention relates to

-   -   the use of compounds I and/or their salts as herbicides;     -   crop protection compositions comprising at least one         1-phenylpyrrolidin-2-one-3-carboxamide of the formula I and/or         at least one agriculturally useful salt of I as active         substances; and     -   methods for controlling unwanted vegetation, which comprises         allowing a herbicidally effective amount of at least one         1-phenylpyrrolidin-2-one-3-carboxamide of the formula I or an         agriculturally useful salt of I to act on plants, their habitat         or on seed.

Depending on the substitution pattern, the compounds of the formula I may contain one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers. The invention provides both the pure enantiomers or diastereomers and their mixtures. The invention also provides tautomers of compounds of the formula I.

If R¹ represents hydrogen, the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula I according to the invention can be present in the form of their agriculturally useful salts. In general, agriculturally useful salts are the salts of those bases or cations which have no adverse effect on the herbicidal action of the compounds I. Thus, suitable basic salts are in particular the salts of the alkali metals, preferably of sodium and potassium, of the alkaline earth metals, preferably of calcium, magnesium and barium, and of the transition metals, preferably of manganese, copper, zinc and iron, and also ammonium salts where the ammonium ion may, if desired, carry one to four C₁-C₄-alkyl substituents, C₁-C₄-hydroxyalkyl substituents, C₁-C₄-alkoxy-C₁-C₄-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, trimethyl-2-hydroxyethylammonium, bis(2-hydroxyethyl)methylammonium, tris(2-hydroxyethyl)ammonium, bis(2-hydroxyethyl)-dimethylammonium, tris(2-hydroxyethyl)methylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

The organic moieties mentioned in the definition of the substituents R¹ to R¹² or as radicals on heterocyclic rings are—like the term halo—collective terms for individual listings of the individual group members. All carbon chains, i.e. all alkyl, haloalkyl, cyanoalkyl, aminoalkyl, aminocarbonylalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, alkynyl and alkenyl moieties, may be straight-chain or branched. Halogenated substituents preferably carry one to five identical or different halogen atoms. The term halo denotes in each case fluorine, chlorine, bromine or iodine.

Examples of other meanings are:

-   -   C₁-C₄-alkyl: for example methyl, ethyl, propyl, 1-methylethyl,         butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;     -   C₁-C₆-alkyl: C₁-C₄-alkyl as mentioned above and also, for         example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,         2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl,         1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl,         3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl,         1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl,         2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,         2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl or         1-ethyl-3-methylpropyl;     -   C₁-C₁₀-alkyl: C₁-C₆-alkyl as mentioned above and also, for         example, n-heptyl, 2-heptyl, 2-methylhexyl, n-octyl,         1-methylheptyl, 2-ethylhexyl, n-nonyl, 2-nonyl, n-decyl,         2-decyl, 2-propylheptyl and the like;     -   C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which         is partially or fully substituted by fluorine, chlorine, bromine         and/or iodine, i.e., for example, chloromethyl, dichloromethyl,         trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,         chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,         2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl,         2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,         2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,         2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl,         3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,         2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl,         2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,         3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl,         heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl,         1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl,         4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;         in particular difluoromethyl, trifluoromethyl;     -   C₁-C₆-haloalkyl: C₁-C₄-haloalkyl as mentioned above and also         5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl,         undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl,         6-iodohexyl or dodecafluorohexyl;     -   C₁-C₂-fluoroalkyl: C₁-C₂-alkyl which carries 1, 2, 3, 4 or 5         fluorine atoms, for example difluoromethyl, trifluoromethyl,         2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,         1,1,2,2-tetrafluoroethyl and pentafluoroethyl;     -   C₁-C₂-fluoroalkoxy: C₁-C₂-alkoxy which carries 1, 2, 3, 4 or 5         fluorine atoms, for example difluoromethoxy, trifluoromethoxy,         2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,         1,1,2,2-tetrafluoroethoxy and pentafluoroethoxy;     -   C₁-C₄-alkoxy: for example methoxy, ethoxy, n-propoxy,         1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or         1,1-dimethylethoxy;     -   C₁-C₆-alkoxy: C₁-C₄-alkoxy as mentioned above and also, for         example, pentoxy, 1-methylbutoxy, 2-methylbutoxy,         3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy,         2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy,         2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,         1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,         2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,         1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,         1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or         1-ethyl-2-methylpropoxy;     -   C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above         which is partially or fully substituted by fluorine, chlorine,         bromine and/or iodine, i.e., for example, OCH₂F, OCHF₂, OCF₃,         OCH₂Cl, OCH(Cl)₂, OC(Cl)₃, chlorofluoromethoxy,         dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy,         2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,         2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,         2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,         2,2,2-trichloroethoxy, OC₂F₅, 2-fluoropropoxy, 3-fluoropropoxy,         2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy,         3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy,         3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,         OCH₂—C₂F₅, OCF₂—C₂F₅, 1-(CH₂F)-2-fluoroethoxy,         1-(CH₂Cl)-2-chloroethoxy, 1-(CH₂Br)-2-bromoethoxy,         4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or         nonafluorobutoxy, preferably OCHF₂ or OCHF₃;     -   C₁-C₄-alkoxy-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by         C₁-C₆-alkoxy—as mentioned above—, i.e., for example, CH₂—OCH₃,         CH₂—OC₂H₅, n-propoxymethyl, CH₂—OCH(CH₃) 2, n-butoxymethyl,         (1-methylpropoxy)methyl, (2-methylpropoxy)methyl, CH₂—OC(CH₃)₃,         2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)ethyl,         2-(1-methylethoxy)ethyl, 2-(n-butoxy)ethyl,         2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl,         2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl,         2-(ethoxy)propyl, 2-(n-propoxy)propyl, 2-(1-methylethoxy)propyl,         2-(n-butoxy)propyl, 2-(1-methylpropoxy)propyl,         2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl,         3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(n-propoxy)propyl,         3-(1-methylethoxy)propyl, 3-(n-butoxy)propyl,         3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,         3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl,         2-(n-propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(n-butoxy)butyl,         2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl,         2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl,         3-(n-propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(n-butoxy)butyl,         3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,         3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl,         4-(n-propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(n-butoxy)butyl,         4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl,         4-(1,1-dimethylethoxy)butyl, 2-(1-methylethoxy)pentyl,         2-(n-butoxy)pentyl, 2-(1-methylpropoxy)pentyl,         2-(2-methylpropoxy)pentyl, 2-(1,1-dimethylethoxy)pentyl,         3-(methoxy)pentyl, 3-(ethoxy)pentyl, 3-(n-propoxy)pentyl,         3-(1-methylethoxy)pentyl, 3-(n-butoxy)pentyl,         3-(1-methylpropoxy)pentyl, 3-(2-methylpropoxy)pentyl,         3-(1,1-dimethylethoxy)pentyl, 4-(methoxy)pentyl,         4-(ethoxy)pentyl, 4-(n-propoxy)pentyl, 4-(1-methylethoxy)pentyl,         4-(n-butoxy)pentyl, 4-(1-methylpropoxy)pentyl,         4-(2-methylpropoxy)pentyl, 4-(1,1-dimethylethoxy)pentyl,         4-(methoxy)pentyl, 5-(ethoxy)pentyl, 5-(n-propoxy)pentyl,         5-(1-methylethoxy)pentyl, 5-(n-butoxy)pentyl,         5-(1-methylpropoxy)pentyl, 5-(2-methylpropoxy)pentyl,         5-(1,1-dimethylethoxy)pentyl, 2-(1-methylethoxy)hexyl,         2-(n-butoxy)hexyl, 2-(1-methylpropoxy)hexyl,         2-(2-methylpropoxy)hexyl, 2-(1,1-dimethylethoxy)hexyl,         3-(methoxy)hexyl, 3-(ethoxy)hexyl, 3-(n-propoxy)hexyl,         3-(1-methylethoxy)hexyl, 3-(n-butoxy)hexyl,         3-(1-methylpropoxy)hexyl, 3-(2-methylpropoxy)hexyl         3-(1,1-dimethylethoxy)hexyl, 4-(methoxy)hexyl, 4-(ethoxy)hexyl,         4-(n-propoxy)hexyl, 4-(1-methylethoxy)hexyl, 4-(n-butoxy)hexyl,         4-(1-methylpropoxy)hexyl, 4-(2-methylpropoxy)hexyl,         4-(1,1-dimethylethoxy)hexyl, 4-(methoxy)hexyl, 5-(ethoxy)hexyl,         5-(n-propoxy)hexyl, 5-(1-methylethoxy)hexyl, 5-(n-butoxy)hexyl,         5-(1-methylpropoxy)hexyl, 5-(2-methylpropoxy)hexyl,         5-(1,1-dimethylethoxy)hexyl, 6-(ethoxy)hexyl,         6-(n-propoxy)hexyl, 6-(1-methylethoxy)hexyl, 6-(n-butoxy)hexyl,         6-(1-methylpropoxy)hexyl, 6-(2-methylpropoxy)hexyl,         6-(1,1-dimethylethoxy)hexyl;     -   C₁-C₄-alkylthio: an alkylsulfanyl radical having 1 to 4 carbon         atoms, for example SCH₃, SC₂H₅, SCH₂—C₂H₅, SCH(CH₃)₂,         n-butylthio, SCH(CH₃)—C₂H₅, SCH₂—CH(CH₃) 2 or SC(CH₃) 3;     -   C₁-C₆-alkylthio: C₁-C₄-alkylthio as mentioned above and also,         for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio,         3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio,         hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio,         1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio,         4-methylpentylthio, 1,1-dimethylbutylthio,         1,2-dimethylbutylthio, 1,3-dimethylbutylthio,         2,2-dimethylbutylthio, 2,3-dimethylbutylthio,         3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio,         1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,         1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio;     -   C₁-C₄-haloalkylthio: a C₁-C₄-alkylthio radical as mentioned         above which is partially or fully substituted by fluorine,         chlorine, bromine and/or iodine, i.e., for example,         fluoromethylthio, difluoromethylthio, trifluoromethylthio,         chlorodifluoromethylthio, bromodifluoromethylthio,         2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio,         2-iodoethylthio, 2,2-difluoroethylthio,         2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio,         2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,         2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio,         2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio,         3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio,         2,2-difluoropropylthio, 2,3-difluoropropylthio,         2,3-dichloropropylthio, 3,3,3-trifluoropropylthio,         3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio,         heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio,         1-(chloromethyl)-2-chloroethylthio,         1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio,         4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio;     -   phenyl-C₁-C₄-alkyl: for example benzyl, 1-phenylethyl,         2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl,         3-phenylprop-1-yl, 1-phenylbut-1-yl, 2-phenylbut-1-yl,         3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl,         2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl,         1-(benzyl)eth-1-yl, 1-(benzyl)-1-(methyl)eth-1-yl or         1-(benzyl)prop-1-yl;     -   C₂-C₆-alkenyl: a monounsaturated aliphatic hydrocarbon radical         having 2 to 6 and in particular 2 to 4 carbon atoms, for example         ethenyl, prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl,         buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-1-en-1-yl,         2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl,         2-methylprop-2-en-1-yl, penten-1-yl, penten-2-yl, penten-3-yl,         penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl,         3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl,         2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl,         1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl,         3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl,         1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl,         1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, hex-1-en-1-yl,         hex-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl,         1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl,         3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl,         1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl,         3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl,         1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl,         3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl,         1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl,         3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl,         1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl,         1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl,         1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl,         1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl,         2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl,         2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl,         3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl,         1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl,         1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl,         2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl,         1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl,         1-ethyl-2-methylprop-1-en-1-yl and         1-ethyl-2-methylprop-2-en-1-yl;     -   C₃-C₈-alkenyl: an aliphatic hydrocarbon radical which contains a         C═C double bond and has 3 to 8, preferably 3 to 6 and in         particular 3 or 4 carbon atoms as mentioned above, which is         preferably not attached via a carbon atom of the double bond,         for example one of the radicals mentioned under C₂-C₆-alkenyl         and also 1-hepten-3-yl, 1-hepten-4-yl, 1-hepten-5-yl,         1-hepten-6-yl, 1-hepten-7-yl, 3-hepten-1-yl, 2-hepten-4-yl,         3-hepten-5-yl, 3-hepten-6-yl, 3-hepten-7-yl, 1-octen-3-yl,         1-octen-4-yl, 1-octen-5-yl, 1-octen-6-yl, 1-octen-7-yl,         1-octen-8-yl, 3-octen-1-yl, 2-octen-1-yl, 2-octen-4-yl,         3-octen-5-yl, 3-octen-6-yl, 3-octen-7-yl, 3-octen-8-yl and the         like;     -   C₂-C₆-haloalkenyl: C₂-C₆-alkenyl as mentioned above which is         partially or fully substituted by fluorine, chlorine, and/or         bromine, i.e., for example, 2-chlorovinyl, 2-chloroallyl,         3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl,         2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl,         3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl,         2,3,3-tribromoallyl and 2,3-dibromobut-2-enyl;     -   C₂-C₆-alkynyl: an aliphatic hydrocarbon radical which contains a         C—C triple bond and has 2 to 6 and in particular 2 to 4 carbon         atoms: for example ethynyl, propargyl (2-propynyl), 1-propynyl,         but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl, pent-1-yn-3-yl,         pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl, pent-2-yn-4-yl,         pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl,         hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl, hex-1-yn-6-yl,         hex-2-yn-1-yl, hex-2-yn-4-yl, hex-2-yn-5-yl, hex-2-yn-6-yl,         hex-3-yn-1-yl, hex-3-yn-2-yl, 3-methylpent-1-yn-3-yl,         3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl,         4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl;     -   C₃-C₁₀-alkynyl: an aliphatic hydrocarbon radical which contains         a triple bond and has 3 to 10, preferably 3 to 6 and in         particular 3 or 4 carbon atoms as mentioned above, which is         preferably not attached via a carbon atom of the triple bond,         for example one of the radicals mentioned under C₂-C₆-alkynyl         and also 1-heptyn-3-yl, 1-heptyn-4-yl, 1-heptyn-5-yl,         1-heptyn-6-yl, 1-heptyn-7-yl, 3-heptyn-1-yl, 2-heptyn-4-yl,         3-heptyn-5-yl, 3-heptyn-6-yl, 3-heptyn-7-yl, 1-octyn-3-yl,         1-octyn-4-yl, 1-octyn-5-yl, 1-octyn-6-yl, 1-octyn-7-yl,         1-octyn-8-yl, 3-octyn-1-yl, 2-octyn-1-yl, 2-octyn-4-yl,         3-octyn-5-yl, 3-octyn-6-yl, 3-octyn-7-yl, 3-octyn-8-yl and the         like;     -   C₃-C₁₀-cycloalkyl: a monocyclic hydrocarbon radical having 3 to         10 carbon atoms, in particular 3 to 8 carbon atoms and         especially 3 to 6 carbon atoms, for example cyclopropyl,         cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl;     -   C₇-C₁₀-polycycloalkyl: a bicyclic, tricyclic or tetracyclic         hydrocarbon radical having 7 to 10 carbon atoms, for example         bicyclo[2.2.1]-hept-1-yl, bicyclo[2.2.1]hept-2-yl,         bicyclo[2.2.1]hept-7-yl, bicyclo[2.2.2]oct-1-yl,         bicyclo[2.2.2]oct-2-yl or adamantan-1-yl;     -   C₃-C₈-cycloalkyl-C₁-C₄-alkyl: C₁-C₄-alkyl which carries a         C₃-C₈-cycloalkyl radical as defined above, for example         cyclopropylmethyl, 1-cyclopropylethyl, 2-cyclopropylethyl,         1-cyclopropylprop-1-yl, 2-cyclopropylprop-1-yl,         3-cyclopropylprop-1-yl, 1-cyclopropylbut-1-yl,         2-cyclopropylbut-1-yl, 3-cyclopropylbut-1-yl,         4-cyclopropylbut-1-yl, 1-cyclopropylbut-2-yl,         2-cyclopropylbut-2-yl, 3-cyclopropylbut-2-yl,         3-cyclopropylbut-2-yl, 4-cyclopropylbut-2-yl,         1-(cyclopropylmethyl)eth-1-yl,         1-(cyclopropylmethyl)-1-(methyl)eth-1-yl,         1-(cyclopropylmethyl)prop-1-yl, cyclobutylmethyl,         1-cyclobutylethyl, 2-cyclobutylethyl, 1-cyclobutylprop-1-yl,         2-cyclobutylprop-1-yl, 3-cyclobutylprop-1-yl,         1-cyclobutylbut-1-yl, 2-cyclobutylbut-1-yl,         3-cyclobutylbut-1-yl, 4-cyclobutylbut-1-yl,         1-cyclobutylbut-2-yl, 2-cyclobutylbut-2-yl,         3-cyclobutylbut-2-yl, 4-cyclobutylbut-2-yl,         1-(cyclobutylmethyl)eth-1-yl,         1-(cyclobutylmethyl)-1-(methyl)eth-1-yl,         1-(cyclobutylmethyl)prop-1-yl, cyclopentylmethyl,         1-cyclopentylethyl, 2-cyclopentylethyl, 1-cyclopentylprop-1-yl,         2-cyclopentylprop-1-yl, 3-cyclopentylprop-1-yl,         1-cyclopentylbut-1-yl, 2-cyclopentylbut-1-yl,         3-cyclopentylbut-1-yl, 4-cyclopentylbut-1-yl,         1-cyclopentylbut-2-yl, 2-cyclopentylbut-2-yl,         3-cyclopentylbut-2-yl, 3-cyclopentylbut-2-yl,         4-cyclopentylbut-2-yl, 1-(cyclopentylmethyl)eth-1-yl,         1-(cyclopentylmethyl)-1-(methyl)eth-1-yl,         1-(cyclopentylmethyl)prop-1-yl, cyclohexylmethyl,         1-cyclohexylethyl, 2-cyclohexylethyl, 1-cyclohexylprop-1-yl,         2-cyclohexylprop-1-yl, 3-cyclohexylprop-1-yl,         1-cyclohexylbut-1-yl, 2-cyclohexylbut-1-yl,         3-cyclohexylbut-1-yl, 4-cyclohexylbut-1-yl,         1-cyclohexylbut-2-yl, 2-cyclohexylbut-2-yl,         3-cyclohexylbut-2-yl, 4-cyclohexylbut-2-yl,         1-(cyclohexylmethyl)eth-1-yl,         1-(cyclohexylmethyl)-1-(methyl)eth-1-yl,         1-(cyclohexylmethyl)prop-1-yl, cycloheptylmethyl,         1-cycloheptylethyl, 2-cycloheptylethyl, 1-cycloheptylprop-1-yl,         2-cycloheptylprop-1-yl, 3-cycloheptylprop-1-yl,         1-cycloheptylbut-1-yl, 2-cycloheptylbut-1-yl,         3-cycloheptylbut-1-yl, 4-cycloheptylbut-1-yl,         1-cycloheptylbut-2-yl, 2-cycloheptylbut-2-yl,         3-cycloheptylbut-2-yl, 4-cycloheptylbut-2-yl,         1-(cycloheptylmethyl)eth-1-yl,         1-(cycloheptylmethyl)-1-(methyl)eth-1-yl,         1-(cycloheptylmethyl)prop-1-yl, cyclooctylmethyl,         1-cyclooctylethyl, 2-cyclooctylethyl, 1-cyclooctylprop-1-yl,         2-cyclooctylprop-1-yl, 3-cyclooctylprop-1-yl,         1-cyclooctylbut-1-yl, 2-cyclooctylbut-1-yl,         3-cyclooctylbut-1-yl, 4-cyclooctylbut-1-yl,         1-cyclooctylbut-2-yl, 2-cyclooctylbut-2-yl,         3-cyclooctylbut-2-yl, 4-cyclooctylbut-2-yl,         1-(cyclooctylmethyl)eth-1-yl,         1-(cyclooctylmethyl)-1-(methyl)eth-1-yl or         1-(cyclooctylmethyl)prop-1-yl, preferably cyclopropylmethyl,         cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl.

C₅-C₁₀-cycloalkenyl: a mono- or bicyclic hydrocarbon radical having 5 to 10 carbon atoms, in particular 5 to 8 carbon atoms and especially 5 to 6 carbon atoms and which contains a C═C double bond, for example cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexen-4-yl, cyclohepten-1-yl, cyclohepten-3-yl, cyclohepten-4-yl, cycloocten-1-yl, cycloocten-3-yl, cycloocten-4-yl, cycloocten-5-yl, bicyclo[2.2.1]hept-2-en-1-yl, bicyclo[2.2.1]hept-2-en-2-yl, bicyclo[2.2.1]hept-2-en-5-yl, bicyclo[2.2.1]hept-2-en-7-yl, bicyclo[2.2.2]oct-2-en-1-yl, bicyclo[2.2.2]oct-2-en-2-yl, bicyclo[2.2.2]oct-2-en-5-yl, bicyclo[2.2.2]oct-2-en-7-yl;

-   -   unsubstituted or substituted phenyl: a phenyl group which is         unsubstituted or carries 1, 2, 3 or 4 substituents, where the         substituents are selected from the group consisting of halogen,         nitro, cyano, OH, alkyl, alkoxy, haloalkyl, haloalkoxy, COOR⁵,         NR⁶R⁷, C(O)NR⁸R⁹;     -   3- to 7-membered heterocyclyl: a heterocyclic radical which has         3, 4, 5, 6 or 7 ring members, where 1, 2 or 3 of the ring         members are heteroatoms selected from the group consisting of         oxygen, nitrogen, sulfur, a group SO₂ and a group NR¹⁰.         Moreover, the heterocycle may optionally contain 1, 2 or 3         carbonyl groups and/or thiocarbonyl groups as ring members. The         heterocycle may furthermore contain a ring-fused unsubstituted         or substituted phenyl ring. The heterocycle may be aromatic         (heteroaryl) or partially or fully saturated.     -   Examples of saturated heterocycles are: oxiran-1-yl,         aziridin-1-yl, oxetan-2-yl, oxetan-3-yl, thietan-2-yl,         thietan-3-yl, azetidin-1-yl, azetidin-2-yl, azetidin-3-yl,         tetrahydrofuran-2-yl, tetrahydrofuran-3-yl,         tetrahydrothiophen-2-yl, tetrahydrothiophen-3-yl,         pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl,         1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl,         1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-oxazolidin-2-yl,         1,3-oxazolidin-3-yl, 1,3-oxazolidin-4-yl, 1,3-oxazolidin-5-yl,         1,2-oxazolidin-2-yl, 1,2-oxazolidin-3-yl, 1,2-oxazolidin-4-yl,         1,2-oxazolidin-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl,         pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-5-yl,         tetrahydropyrazol-1-yl, tetrahydropyrazol-3-yl,         tetrahydropyrazol-4-yl, tetrahydropyran-2-yl,         tetrahydropyran-3-yl, tetrahydropyran-4-yl,         tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl,         tetrahydropyran-4-yl, piperidin-1-yl, piperidin-2-yl,         piperidin-3-yl, piperidin-4-yl, 1,3-dioxan-2-yl,         1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl,         1,3-oxathian-2-yl, 1,3-oxathian-4-yl, 1,3-oxathian-5-yl,         1,3-oxathian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathian-3-yl,         morpholin-2-yl, morpholin-3-yl, morpholin-4-yl,         hexahydropyridazin-1-yl, hexahydropyridazin-3-yl,         hexahydropyridazin-4-yl, hexahydropyrimidin-1-yl,         hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl,         hexahydropyrimidin-5-yl, piperazin-1-yl, piperazin-2-yl,         piperazin-3-yl, hexahydro-1,3,5-triazin-1-yl,         hexahydro-1,3,5-triazin-2-yl, oxepan-2-yl, oxepan-3-yl,         oxepan-4-yl, thiepan-2-yl, thiepan-3-yl, thiepan-4-yl,         1,3-dioxepan-2-yl, 1,3-dioxepan-4-yl, 1,3-dioxepan-5-yl,         1,3-dioxepan-6-yl, 1,3-dithiepan-2-yl, 1,3-dithiepan-4-yl,         1,3-dithiepan-5-yl, 1,3-dithiepan-6-yl, 1,4-dioxepan-2-yl,         1,4-dioxepan-7-yl, hexahydroazepin-1-yl, hexahydroazepin-2-yl,         hexahydroazepin-3-yl, hexahydroazepin-4-yl,         hexahydro-1,3-diazepin-1-yl, hexahydro-1,3-diazepin-2-yl,         hexahydro-1,3-diazepin-4-yl, hexahydro-1,4-diazepin-1-yl and         hexahydro-1,4-diazepin-2-yl;     -   Examples of unsaturated heterocycles are:     -   dihydrofuran-2-yl, 1,2-oxazolin-3-yl, 1,2-oxazolin-5-yl,         1,3-oxazolin-2-yl;     -   Examples of aromatic heterocyclyl are the 5- and 6-membered         aromatic, heterocyclic radicals, for example furyl, such as         2-furyl and 3-furyl, thienyl, such as 2-thienyl and 3-thienyl,         pyrrolyl, such as 2-pyrrolyl and 3-pyrrolyl, isoxazolyl, such as         3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl, such         as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl,         such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, oxazolyl, such         as 2-oxazolyl, 4-oxazolyl and 5-oxazolyl, thiazolyl, such as         2-thiazolyl, 4-thiazolyl and 5-thiazolyl, imidazolyl, such as         2-imidazolyl and 4-imidazolyl, oxadiazolyl, such as         1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and         1,3,4-oxadiazol-2-yl, thiadiazolyl, such as         1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl and         1,3,4-thiadiazol-2-yl, triazolyl, such as 1,2,4-triazol-1-yl,         1,2,4-triazol-3-yl and 1,2,4-triazol-4-yl, pyridinyl, such as         2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl, such as         3-pyridazinyl and 4-pyridazinyl, pyrimidinyl, such as         2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl, furthermore         2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl, in         particular pyridyl, pyrimidyl, furanyl and thienyl.

If the radicals R² and R³ together with the nitrogen atom to which they are attached form a saturated heterocycle, n is preferably 0. In this case, the saturated heterocycle is selected, for example, from the group consisting of 1,3-oxazolidin-3-yl, 1,2-oxazolidin-2-yl, pyrrolidin-1-yl, pyrrolidin-2-on-1-yl, tetrahydropyrazol-1-yl, 2-methyltetrahydropyrazol-1-yl, piperidin-1-yl, piperidin-2-on-1-yl, morpholin-4-yl, hexahydropyrimidin-1-yl, piperazin-1-yl, 4-methylpiperazin-1-yl, hexahydro-1,3,5-triazin-1-yl, 3,5-dimethyltriazin-1-yl, hexahydroazepin-1-yl, hexahydroazepin-2-on-1-yl, hexahydro-1,3-diazepin-1-yl, hexahydro-1,4-diazepin-1-yl, in particular from the group consisting of pyrrolidin-1-yl, piperidin-1-yl and morpholin-4-yl.

If two adjacent radicals R^(a) to R^(e) together with the atoms to which they are attached form a 5-, 6- or 7-membered saturated or unsaturated ring which may contain one or two heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur and a group NR¹⁰ as ring-forming atom(s) and/or may carry one, two, three or four radicals selected from the group consisting of halogen and C₁-C₄-alkyl, two adjacent radicals R^(a) to R^(e), for example R^(b) and R^(c) or R^(c) and R^(d), together are a 3-, 4- or 5-membered saturated or unsaturated carbon chain in which one or two non-adjacent carbon atoms of the chain may be replaced by heteroatoms selected from the group consisting of O, N, a group NR¹⁰ and S and in which the carbon atoms of the chain may carry one, two, three or four substituents selected from the group consisting of halogen and C₁-C₄-alkyl. For example, two adjacent radicals R^(a) to R^(e) may be a chain of the formula —O—CH₂—O—, —O—(CH₂)₂—O—, —O—(CH₂)₂—, —O—(CH₂)₃—, —(CH₂)₃—, —(CH₂)₄— or —(CH₂)₅—

With a view to the use of the compounds of the formula I according to the invention as herbicides, the variables R¹, R², R³, X, Y, A, n, R^(a), R^(b), R^(c), R^(d) and R^(e) are preferably as defined below, independently of one another and in particular in combination:

-   R¹ is hydrogen, OH, Cl, Br, C₁-C₆-alkyl or OC(O)R⁴, particularly     preferably hydrogen; -   R² is C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl,     C₃-C₈-cycloalkyl, C₅-C₈-cycloalkenyl or     C₃-C₈-cycloalkyl-C₁-C₄-alkyl, where C₁-C₁₀-alkyl and     C₃-C₈-cycloalkyl may be partially or fully halogenated and/or may     carry one or two radicals selected from the group consisting of     C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkylthio,     C₁-C₄-haloalkylthio, unsubstituted or substituted phenyl, COOR⁵,     NR⁶R⁷, C(O)NR⁸R⁹, phenyl which may be unsubstituted or substituted     by 1, 2 or 3 substituents selected from the group consisting of     halogen, nitro, OH, CN, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-haloalkoxy,     C₁-C₆-alkylthio, C₁-C₄-haloalkylthio, unsubstituted or substituted     phenyl, COOR⁵, NR⁶R⁷, C(O)NR⁸R⁹. In particular, R² is C₁-C₆-alkyl,     C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₅-C₆-cycloalkenyl,     C₃-C₆-cycloalkyl-C₁-C₄-alkyl or unsubstituted or substituted phenyl,     where C₁-C₆-alkyl and C₃-C₆-cycloalkyl may be partially or fully     halogenated and/or may carry one or two, in particular one, radical     selected from the group consisting of C₁-C₆-alkoxy,     C₁-C₄-haloalkoxy, C₁-C₆-alkylthio, C₁-C₄-haloalkylthio,     unsubstituted or substituted phenyl, COOR⁵, NR⁶R⁷, C(O)NR⁸R⁹.     Particularly preferably, R² is C₁-C₆-alkyl, C₃-C₈-cycloalkyl,     unsubstituted or substituted phenyl, phenylalkyl or     C₃-C₈-cycloalkyl-C₁-C₄-alkyl; -   R³ is hydrogen or C₁-C₆-alkyl; -   X is oxygen; -   Y is oxygen; and -   A if present, is oxygen, a group N—R¹², where R¹²=hydrogen or alkyl,     or a group SO₂; -   n is 0; -   R^(a), R^(b), R^(c), R^(d), R^(e) are hydrogen, halogen, CN,     C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, in     particular halogen, CN, C₁-C₄-alkyl, C₁-C₂-fluoroalkyl and     C₁-C₂-fluoroalkoxy and especially fluorine, chlorine, bromine, CN,     C₁-C₄-alkyl, methoxy, CF₃, CHF₂, OCF₃ and OCHF₂.

With a view to the use as herbicides, preference is given to 1-phenylpyrrolidin-2-one-3-carboxamides of the formula I according to the invention where not more than 3 of the radicals R^(a), R^(b), R^(c), R^(d) and R^(e) and in particular 3 or 4 of the abovementioned radicals are different from hydrogen. Particular preference is given to 1-phenylpyrrolidin-2-one-3-carboxamides of the formula I where at least R^(b) and/or R^(d) are different from hydrogen. In this case, the other radicals R^(a)-R^(e), at least one of the radicals R^(a) and R^(e) and especially both radicals R^(a) and R^(e) are particularly preferably hydrogen. Particular preference is also given to compounds of the formula I in which R^(b) and R^(c) or R^(d) and R^(c) are different from hydrogen and the other radicals of the radicals R^(a)-R^(e) are hydrogen. Another preferred embodiment of the invention relates to compounds in which the radicals R^(a) and R^(e) or R^(a) and R^(b) or R^(a) and R^(c) are different from hydrogen and the other radicals of the radicals R^(a)-R^(e) are hydrogen.

Preferred radicals R^(a), R^(b), R^(c), R^(d), R^(e) are, in addition to hydrogen, the substituents halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, in particular halogen, CN, C₁-C₄-alkyl, C₁-C₂-fluoroalkyl and C₁-C₂-fluoroalkoxy and especially fluorine, chlorine, bromine, CN, C₁-C₄-alkyl, methoxy, CF₃, CHF₂, OCF₃ and OCHF₂.

A particularly preferred group of compounds of the formula I are those compounds in which R^(a) and R^(e) are hydrogen. Here, the radical

denotes, for example, a group of the formulae Q1 to Q31:

Another preferred group of compounds of the formula I are those compounds in which R^(a) and, if appropriate, one of the radicals R^(b), R^(c) or R^(e) are different from hydrogen and the other radicals R^(a)-R^(e) are hydrogen. Here, the radical

denotes, for example, a group of the formulae Q32 to Q39:

Particular preference is given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ia (≡I where R^(a)═R^(b)═H, X═O, Y═O, R¹═H, R³═CH₃ and n=0) where R^(b), R^(c), R^(d) and R² have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ia.1 to Ia.1717 in which the variables R^(b), R^(c), R^(d) and R² together have the meanings given in one row of Table 1. TABLE 1 (Ia)

No. R^(b) R^(c) R^(d) R² 1. Cl H H H 2. Br H H H 3. F H H H 4. CH₃ H H H 5. C₂H₅ H H H 6. CH(CH₃)₂ H H H 7. OCH₃ H H H 8. CN H H H 9. CF₃ H H H 10. OCF₃ H H H 11. OCHF₂ H H H 12. Cl H H CH₃ 13. Br H H CH₃ 14. F H H CH₃ 15. CH₃ H H CH₃ 16. C₂H₅ H H CH₃ 17. CH(CH₃)₂ H H CH₃ 18. OCH₃ H H CH₃ 19. CN H H CH₃ 20. CF₃ H H CH₃ 21. OCF₃ H H CH₃ 22. OCHF₂ H H CH₃ 23. Cl H H C₂H₅ 24. Br H H C₂H₅ 25. F H H C₂H₅ 26. CH₃ H H C₂H₅ 27. C₂H₅ H H C₂H₅ 28. CH(CH₃)₂ H H C₂H₅ 29. OCH₃ H H C₂H₅ 30. CN H H C₂H₅ 31. CF₃ H H C₂H₅ 32. OCF₃ H H C₂H₅ 33. OCHF₂ H H C₂H₅ 34. Cl H H n-C₃H₇ 35. Br H H n-C₃H₇ 36. F H H n-C₃H₇ 37. CH₃ H H n-C₃H₇ 38. C₂H₅ H H n-C₃H₇ 39. CH(CH₃)₂ H H n-C₃H₇ 40. OCH₃ H H n-C₃H₇ 41. CN H H n-C₃H₇ 42. CF₃ H H n-C₃H₇ 43. OCF₃ H H n-C₃H₇ 44. OCHF₂ H H n-C₃H₇ 45. Cl H H CH(CH₃)₂ 46. Br H H CH(CH₃)₂ 47. F H H CH(CH₃)₂ 48. CH₃ H H CH(CH₃)₂ 49. C₂H₅ H H CH(CH₃)₂ 50. CH(CH₃)₂ H H CH(CH₃)₂ 51. OCH₃ H H CH(CH₃)₂ 52. CN H H CH(CH₃)₂ 53. CF₃ H H CH(CH₃)₂ 54. OCF₃ H H CH(CH₃)₂ 55. OCHF₂ H H CH(CH₃)₂ 56. Cl H H n-C₄H₉ 57. Br H H n-C₄H₉ 58. F H H n-C₄H₉ 59. CH₃ H H n-C₄H₉ 60. C₂H₅ H H n-C₄H₉ 61. CH(CH₃)₂ H H n-C₄H₉ 62. OCH₃ H H n-C₄H₉ 63. CN H H n-C₄H₉ 64. CF₃ H H n-C₄H₉ 65. OCF₃ H H n-C₄H₉ 66. OCHF₂ H H n-C₄H₉ 67. Cl H H C(CH₃)₃ 68. Br H H C(CH₃)₃ 69. F H H C(CH₃)₃ 70. CH₃ H H C(CH₃)₃ 71. C₂H₅ H H C(CH₃)₃ 72. CH(CH₃)₂ H H C(CH₃)₃ 73. OCH₃ H H C(CH₃)₃ 74. CN H H C(CH₃)₃ 75. CF₃ H H C(CH₃)₃ 76. OCF₃ H H C(CH₃)₃ 77. OCHF₂ H H C(CH₃)₃ 78. Cl H H C₆H₅ 79. Br H H C₆H₅ 80. F H H C₆H₅ 81. CH₃ H H C₆H₅ 82. C₂H₅ H H C₆H₅ 83. CH(CH₃)₂ H H C₆H₅ 84. OCH₃ H H C₆H₅ 85. CN H H C₆H₅ 86. CF₃ H H C₆H₅ 87. OCF₃ H H C₆H₅ 88. OCHF₂ H H C₆H₅ 89. Cl H H cyclopropyl 90. Br H H cyclopropyl 91. F H H cyclopropyl 92. CH₃ H H cyclopropyl 93. C₂H₅ H H cyclopropyl 94. CH(CH₃)₂ H H cyclopropyl 95. OCH₃ H H cyclopropyl 96. CN H H cyclopropyl 97. CF₃ H H cyclopropyl 98. OCF₃ H H cyclopropyl 99. OCHF₂ H H cyclopropyl 100. Cl H H CH₂-cyclopropyl 101. Br H H CH₂-cyclopropyl 102. F H H CH₂-cyclopropyl 103. CH₃ H H CH₂-cyclopropyl 104. C₂H₅ H H CH₂-cyclopropyl 105. CH(CH₃)₂ H H CH₂-cyclopropyl 106. OCH₃ H H CH₂-cyclopropyl 107. CN H H CH₂-cyclopropyl 108. CF₃ H H CH₂-cyclopropyl 109. OCF₃ H H CH₂-cyclopropyl 110. OCHF₂ H H CH₂-cyclopropyl 111. Cl H H cyclobutyl 112. Br H H cyclobutyl 113. F H H cyclobutyl 114. CH₃ H H cyclobutyl 115. C₂H₅ H H cyclobutyl 116. CH(CH₃)₂ H H cyclobutyl 117. OCH₃ H H cyclobutyl 118. CN H H cyclobutyl 119. CF₃ H H cyclobutyl 120. OCF₃ H H cyclobutyl 121. OCHF₂ H H cyclobutyl 122. Cl H H cyclopentyl 123. Br H H cyclopentyl 124. F H H cyclopentyl 125. CH₃ H H cyclopentyl 126. C₂H₅ H H cyclopentyl 127. CH(CH₃)₂ H H cyclopentyl 128. OCH₃ H H cyclopentyl 129. CN H H cyclopentyl 130. CF₃ H H cyclopentyl 131. OCF₃ H H cyclopentyl 132. OCHF₂ H H cyclopentyl 133. Cl H H cyclohexyl 134. Br H H cyclohexyl 135. F H H cyclohexyl 136. CH₃ H H cyclohexyl 137. C₂H₅ H H cyclohexyl 138. CH(CH₃)₂ H H cyclohexyl 139. OCH₃ H H cyclohexyl 140. CN H H cyclohexyl 141. CF₃ H H cyclohexyl 142. OCF₃ H H cyclohexyl 143. OCHF₂ H H cyclohexyl 144. H Cl H H 145. H Br H H 146. H F H H 147. H CH₃ H H 148. H C₂H₅ H H 149. H CH(CH₃)₂ H H 150. H OCH₃ H H 151. H CN H H 152. H CF₃ H H 153. H OCF₃ H H 154. H OCHF₂ H H 155. H Cl H CH₃ 156. H Br H CH₃ 157. H F H CH₃ 158. H CH₃ H CH₃ 159. H C₂H₅ H CH₃ 160. H CH(CH₃)₂ H CH₃ 161. H OCH₃ H CH₃ 162. H CN H CH₃ 163. H CF₃ H CH₃ 164. H OCF₃ H CH₃ 165. H OCHF₂ H CH₃ 166. H Cl H C₂H₅ 167. H Br H C₂H₅ 168. H F H C₂H₅ 169. H CH₃ H C₂H₅ 170. H C₂H₅ H C₂H₅ 171. H CH(CH₃)₂ H C₂H₅ 172. H OCH₃ H C₂H₅ 173. H CN H C₂H₅ 174. H CF₃ H C₂H₅ 175. H OCF₃ H C₂H₅ 176. H OCHF₂ H C₂H₅ 177. H Cl H n-C₃H₇ 178. H Br H n-C₃H₇ 179. H F H n-C₃H₇ 180. H CH₃ H n-C₃H₇ 181. H C₂H₅ H n-C₃H₇ 182. H CH(CH₃)₂ H n-C₃H₇ 183. H OCH₃ H n-C₃H₇ 184. H CN H n-C₃H₇ 185. H CF₃ H n-C₃H₇ 186. H OCF₃ H n-C₃H₇ 187. H OCHF₂ H n-C₃H₇ 188. H Cl H CH(CH₃)₂ 189. H Br H CH(CH₃)₂ 190. H F H CH(CH₃)₂ 191. H CH₃ H CH(CH₃)₂ 192. H C₂H₅ H CH(CH₃)₂ 193. H CH(CH₃)₂ H CH(CH₃)₂ 194. H OCH₃ H CH(CH₃)₂ 195. H CN H CH(CH₃)₂ 196. H CF₃ H CH(CH₃)₂ 197. H OCF₃ H CH(CH₃)₂ 198. H OCHF₂ H CH(CH₃)₂ 199. H Cl H n-C₄H₉ 200. H Br H n-C₄H₉ 201. H F H n-C₄H₉ 202. H CH₃ H n-C₄H₉ 203. H C₂H₅ H n-C₄H₉ 204. H CH(CH₃)₂ H n-C₄H₉ 205. H OCH₃ H n-C₄H₉ 206. H CN H n-C₄H₉ 207. H CF₃ H n-C₄H₉ 208. H OCF₃ H n-C₄H₉ 209. H OCHF₂ H n-C₄H₉ 210. H Cl H C(CH₃)₃ 211. H Br H C(CH₃)₃ 212. H F H C(CH₃)₃ 213. H CH₃ H C(CH₃)₃ 214. H C₂H₅ H C(CH₃)₃ 215. H CH(CH₃)₂ H C(CH₃)₃ 216. H OCH₃ H C(CH₃)₃ 217. H CN H C(CH₃)₃ 218. H CF₃ H C(CH₃)₃ 219. H OCF₃ H C(CH₃)₃ 220. H OCHF₂ H C(CH₃)₃ 221. H Cl H C₆H₅ 222. H Br H C₆H₅ 223. H F H C₆H₅ 224. H CH₃ H C₆H₅ 225. H C₂H₅ H C₆H₅ 226. H CH(CH₃)₂ H C₆H₅ 227. H OCH₃ H C₆H₅ 228. H CN H C₆H₅ 229. H CF₃ H C₆H₅ 230. H OCF₃ H C₆H₅ 231. H OCHF₂ H C₆H₅ 232. H Cl H cyclopropyl 233. H Br H cyclopropyl 234. H F H cyclopropyl 235. H CH₃ H cyclopropyl 236. H C₂H₅ H cyclopropyl 237. H CH(CH₃)₂ H cyclopropyl 238. H OCH₃ H cyclopropyl 239. H CN H cyclopropyl 240. H CF₃ H cyclopropyl 241. H OCF₃ H cyclopropyl 242. H OCHF₂ H cyclopropyl 243. H Cl H CH₂-cyclopropyl 244. H Br H CH₂-cyclopropyl 245. H F H CH₂-cyclopropyl 246. H CH₃ H CH₂-cyclopropyl 247. H C₂H₅ H CH₂-cyclopropyl 248. H CH(CH₃)₂ H CH₂-cyclopropyl 249. H OCH₃ H CH₂-cyclopropyl 250. H CN H CH₂-cyclopropyl 251. H CF₃ H CH₂-cyclopropyl 252. H OCF₃ H CH₂-cyclopropyl 253. H OCHF₂ H CH₂-cyclopropyl 254. H Cl H cyclobutyl 255. H Br H cyclobutyl 256. H F H cyclobutyl 257. H CH₃ H cyclobutyl 258. H C₂H₅ H cyclobutyl 259. H CH(CH₃)₂ H cyclobuty). 260. H OCH₃ H cyclobutyl 261. H CN H cyclobutyl 262. H CF₃ H cyclobutyl 263. H OCF₃ H cyclobutyl 264. H OCHF₂ H cyclobutyl 265. H Cl H cyclopentyl 266. H Br H cyclopentyl 267. H F H cyclopentyl 268. H CH₃ H cyclopentyl 269. H C₂H₅ H cyclopentyl 270. H CH(CH₃)₂ H cyclopentyl 271. H OCH₃ H cyclopentyl 272. H CN H cyclopentyl 273. H CF₃ H cyclopentyl 274. H OCF₃ H cyclopentyl 275. H OCHF₂ H cyclopentyl 276. H Cl H cyclohexyl 277. H Br H cyclohexyl 278. H F H cyclohexyl 279. H CH₃ H cyclohexyl 280. H C₂H₅ H cyclohexyl 281. H CH(CH₃)₂ H cyclohexyl 282. H OCH₃ H cyclohexyl 283. H CN H cyclohexyl 284. H CF₃ H cyclohexyl 285. H OCF₃ H cyclohexyl 286. H OCHF₂ H cyclohexyl 287. CF₃ Br H H 288. CF₃ OCH₃ H H 289. CF₃ Cl H H 290. CF₃ F H H 291. CF₃ CH₃ H H 292. CF₃ C₂H₅ H H 293. CF₃ CF₃ H H 294. CF₃ OCF₃ H H 295. CF₃ OCHF₂ H H 296. CF₃ Br H CH₃ 297. CF₃ OCH₃ H CH₃ 298. CF₃ Cl H CH₃ 299. CF₃ F H CH₃ 300. CF₃ CH₃ H CH₃ 301. CF₃ C₂H₅ H CH₃ 302. CF₃ CF₃ H CH₃ 303. CF₃ OCF₃ H CH₃ 304. CF₃ OCHF₂ H CH₃ 305. CF₃ Br H C₂H₅ 306. CF₃ OCH₃ H C₂H₅ 307. CF₃ Cl H C₂H₅ 308. CF₃ F H C₂H₅ 309. CF₃ CH₃ H C₂H₅ 310. CF₃ C₂H₅ H C₂H₅ 311. CF₃ CF₃ H C₂H₅ 312. CF₃ OCF₃ H C₂H₅ 313. CF₃ OCHF₂ H C₂H₅ 314. CF₃ Br H n-C₃H₇ 315. CF₃ OCH₃ H n-C₃H₇ 316. CF₃ Cl H n-C₃H₇ 317. CF₃ F H n-C₃H₇ 318. CF₃ CH₃ H n-C₃H₇ 319. CF₃ C₂H₅ H n-C₃H₇ 320. CF₃ CF₃ H n-C₃H₇ 321. CF₃ OCF₃ H n-C₃H₇ 322. CF₃ OCHF₂ H n-C₃H₇ 323. CF₃ Br H CH(CH₃)₂ 324. CF₃ OCH₃ H CH(CH₃)₂ 325. CF₃ Cl H CH(CH₃)₂ 326. CF₃ F H CH(CH₃)₂ 327. CF₃ CH₃ H CH(CH₃)₂ 328. CF₃ C₂H₅ H CH(CH₃)₂ 329. CF₃ CF₃ H CH(CH₃)₂ 330. CF₃ OCF₃ H CH(CH₃)₂ 331. CF₃ OCHF₂ H CH(CH₃)₂ 332. CF₃ Br H n-C₄H₉ 333. CF₃ OCH₃ H n-C₄H₉ 334. CF₃ Cl H n-C₄H₉ 335. CF₃ F H n-C₄H₉ 336. CF₃ CH₃ H n-C₄H₉ 337. CF₃ C₂H₅ H n-C₄H₉ 338. CF₃ CF₃ H n-C₄H₉ 339. CF₃ OCF₃ H n-C₄H₉ 340. CF₃ OCHF₂ H n-C₄H₉ 341. CF₃ Br H C(CH₃)₃ 342. CF₃ OCH₃ H C(CH₃)₃ 343. CF₃ Cl H C(CH₃)₃ 344. CF₃ F H C(CH₃)₃ 345. CF₃ CH₃ H C(CH₃)₃ 346. CF₃ C₂H₅ H C(CH₃)₃ 347. CF₃ CF₃ H C(CH₃)₃ 348. CF₃ OCF₃ H C(CH₃)₃ 349. CF₃ OCHF₂ H C(CH₃)₃ 350. CF₃ Br H C₆H₅ 351. CF₃ OCH₃ H C₆H₅ 352. CF₃ Cl H C₆H₅ 353. CF₃ F H C₆H₅ 354. CF₃ CH₃ H C₆H₅ 355. CF₃ C₂H₅ H C₆H₅ 356. CF₃ CF₃ H C₆H₅ 357. CF₃ OCF₃ H C₆H₅ 358. CF₃ OCHF₂ H C₆H₅ 359. CF₃ Br H cyclopropyl 360. CF₃ OCH₃ H cyclopropyl 361. CF₃ Cl H cyclopropyl 362. CF₃ F H cyclopropyl 363. CF₃ CH₃ H cyclopropyl 364. CF₃ C₂H₅ H cyclopropyl 365. CF₃ CF₃ H cyclopropyl 366. CF₃ OCF₃ H cyclopropyl 367. CF₃ OCHF₂ H cyclopropyl 368. CF₃ Br H CH₂-cyclopropyl 369. CF₃ OCH₃ H CH₂-cyclopropyl 370. CF₃ Cl H CH₂-cyclopropyl 371. CF₃ F H CH₂-cyclopropyl 372. CF₃ CH₃ H CH₂-cyclopropyl 373. CF₃ C₂H₅ H CH₂-cyclopropyl 374. CF₃ CF₃ H CH₂-cyclopropyl 375. CF₃ OCF₃ H CH₂-cyclopropyl 376. CF₃ OCHF₂ H CH₂-cyclopropyl 377. CF₃ Br H cyclobutyl 378. CF₃ OCH₃ H cyclobutyl 379. CF₃ Cl H cyclobutyl 380. CF₃ F H cyclobutyl 381. CF₃ CH₃ H cyclobutyl 382. CF₃ C₂H₅ H cyclobutyl 383. CF₃ CF₃ H cyclobutyl 384. CF₃ OCF₃ H cyclobutyl 385. CF₃ OCHF₂ H cyclobutyl 386. CF₃ Br H cyclopentyl 387. CF₃ OCH₃ H cyclopentyl 388. CF₃ Cl H cyclopentyl 389. CF₃ F H cyclopentyl 390. CF₃ CH₃ H cyclopentyl 391. CF₃ C₂H₅ H cyclopentyl 392. CF₃ CF₃ H cyclopentyl 393. CF₃ OCF₃ H cyclopentyl 394. CF₃ OCHF₂ H cyclopentyl 395. CF₃ Br H cyclohexyl 396. CF₃ OCH₃ H cyclohexyl 397. CF₃ Cl H cyclohexyl 398. CF₃ F H cyclohexyl 399. CF₃ CH₃ H cyclohexyl 400. CF₃ C₂H₅ H cyclohexyl 401. CF₃ CF₃ H cyclohexyl 402. CF₃ OCF₃ H cyclohexyl 403. CF₃ OCHF₂ H cyclohexyl 404. CF₃ H Br H 405. CF₃ H OCH₃ H 406. CF₃ H Cl H 407. CF₃ H F H 408. CF₃ H CH₃ H 409. CF₃ H C₂H₅ H 410. CF₃ H CF₃ H 411. CF₃ H OCF₃ H 412. CF₃ H OCHF₂ H 413. CF₃ H Br CH₃ 414. CF₃ H OCH₃ CH₃ 415. CF₃ H Cl CH₃ 416. CF₃ H F CH₃ 417. CF₃ H CH₃ CH₃ 418. CF₃ H C₂H₅ CH₃ 419. CF₃ H CF₃ CH₃ 420. CF₃ H OCF₃ CH₃ 421. CF₃ H OCHF₂ CH₃ 422. CF₃ H Br C₂H₅ 423. CF₃ H OCH₃ C₂H₅ 424. CF₃ H Cl C₂H₅ 425. CF₃ H F C₂H₅ 426. CF₃ H CH₃ C₂H₅ 427. CF₃ H C₂H₅ C₂H₅ 428. CF₃ H CF₃ C₂H₅ 429. CF₃ H OCF₃ C₂H₅ 430. CF₃ H OCHF₂ C₂H₅ 431. CF₃ H Br n-C₃H₇ 432. CF₃ H OCH₃ n-C₃H₇ 433. CF₃ H Cl n-C₃H₇ 434. CF₃ H F n-C₃H₇ 435. CF₃ H CH₃ n-C₃H₇ 436. CF₃ H C₂H₅ n-C₃H₇ 437. CF₃ H CF₃ n-C₃H₇ 438. CF₃ H OCF₃ n-C₃H₇ 439. CF₃ H OCHF₂ n-C₃H₇ 440. CF₃ H Br CH(CH₃)₂ 441. CF₃ H OCH₃ CH(CH₃)₂ 442. CF₃ H Cl CH(CH₃)₂ 443. CF₃ H F CH(CH₃)₂ 444. CF₃ H CH₃ CH(CH₃)₂ 445. CF₃ H C₂H₅ CH(CH₃)₂ 446. CF₃ H CF₃ CH(CH₃)₂ 447. CF₃ H OCF₃ CH(CH₃)₂ 448. CF₃ H OCHF₂ CH(CH₃)₂ 449. CF₃ H Br n-C₄H₉ 450. CF₃ H OCH₃ n-C₄H₉ 451. CF₃ H Cl n-C₄H₉ 452. CF₃ H F n-C₄H₉ 453. CF₃ H CH₃ n-C₄H₉ 454. CF₃ H C₂H₅ n-C₄H₉ 455. CF₃ H CF₃ n-C₄H₉ 456. CF₃ H OCF₃ n-C₄H₉ 457. CF₃ H OCHF₂ n-C₄H₉ 458. CF₃ H Br C(CH₃)₃ 459. CF₃ H OCH₃ C(CH₃)₃ 460. CF₃ H Cl C(CH₃)₃ 461. CF₃ H F C(CH₃)₃ 462. CF₃ H CH₃ C(CH₃)₃ 463. CF₃ H C₂H₅ C(CH₃)₃ 464. CF₃ H CF₃ C(CH₃)₃ 465. CF₃ H OCF₃ C(CH₃)₃ 466. CF₃ H OCHF₂ C(CH₃)₃ 467. CF₃ H Br C₆H₅ 468. CF₃ H OCH₃ C₆H₅ 469. CF₃ H Cl C₆H₅ 470. CF₃ H F C₆H₅ 471. CF₃ H CH₃ C₆H₅ 472. CF₃ H C₂H₅ C₆H₅ 473. CF₃ H CF₃ C₆H₅ 474. CF₃ H OCF₃ C₆H₅ 475. CF₃ H OCHF₂ C₆H₅ 476. CF₃ H Br cyclopropyl 477. CF₃ H OCH₃ cyclopropyl 478. CF₃ H Cl cyclopropyl 479. CF₃ H F cyclopropyl 480. CF₃ H CH₃ cyclopropyl 481. CF₃ H C₂H₅ cyclopropyl 482. CF₃ H CF₃ cyclopropyl 483. CF₃ H OCF₃ cyclopropyl 484. CF₃ H OCHF₂ cyclopropyl 485. CF₃ H Br CH₂-cyclopropyl 486. CF₃ H OCH₃ CH₂-cyclopropyl 487. CF₃ H Cl CH₂-cyclopropyl 488. CF₃ H F CH₂-cyclopropyl 489. CF₃ H CH₃ CH₂-cyclopropyl 490. CF₃ H C₂H₅ CH₂-cyclopropyl 491. CF₃ H CF₃ CH₂-cyclopropyl 492. CF₃ H OCF₃ CH₂-cyclopropyl 493. CF₃ H OCHF₂ CH₂-cyclopropyl 494. CF₃ H Br cyclobutyl 495. CF₃ H OCH₃ cyclobutyl 496. CF₃ H Cl cyclobutyl 497. CF₃ H F cyclobutyl 498. CF₃ H CH₃ cyclobutyl 499. CF₃ H C₂H₅ cyclobutyl 500. CF₃ H CF₃ cyclobutyl 501. CF₃ H OCF₃ cyclobutyl 502. CF₃ H OCHF₂ cyclobutyl 503. CF₃ H Br cyclopentyl 504. CF₃ H OCH₃ cyclopentyl 505. CF₃ H Cl cyclopentyl 506. CF₃ H F cyclopentyl 507. CF₃ H CH₃ cyclopentyl 508. CF₃ H C₂H₅ cyclopentyl 509. CF₃ H CF₃ cyclopentyl 510. CF₃ H OCF₃ cyclopentyl 511. CF₃ H OCHF₂ cyclopentyl 512. CF₃ H Br cyclohexyl 513. CF₃ H OCH₃ cyclohexyl 514. CF₃ H Cl cyclohexyl 515. CF₃ H F cyclohexyl 516. CF₃ H CH₃ cyclohexyl 517. CF₃ H C₂H₅ cyclohexyl 518. CF₃ H CF₃ cyclohexyl 519. CF₃ H OCF₃ cyclohexyl 520. CF₃ H OCHF₂ cyclohexyl 521. OCF₃ Br H H 522. OCF₃ OCH₃ H H 523. OCF₃ Cl H H 524. OCF₃ F H H 525. OCF₃ CH₃ H H 526. OCF₃ C₂H₅ H H 527. OCF₃ CF₃ H H 528. OCF₃ OCF₃ H H 529. OCF₃ OCHF₂ H H 530. OCF₃ Br H CH₃ 531. OCF₃ OCH₃ H CH₃ 532. OCF₃ Cl H CH₃ 533. OCF₃ F H CH₃ 534. OCF₃ Cl3 H CH₃ 535. OCF₃ C₂H₅ H CH₃ 536. OCF₃ CF₃ H CH₃ 537. OCF₃ OCF₃ H CH₃ 538. OCF₃ OCHF₂ H CH₃ 539. OCF₃ Br H C₂H₅ 540. OCF₃ OCH₃ H C₂H₅ 541. OCF₃ Cl H C₂H₅ 542. OCF₃ F H C₂H₅ 543. OCF₃ CH₃ H C₂H₅ 544. OCF₃ C₂H₅ H C₂H₅ 545. OCF₃ CF₃ H C₂H₅ 546. OCF₃ OCF₃ H C₂H₅ 547. OCF₃ OCHF₂ H C₂H₅ 548. OCF₃ Br H n-C₃H₇ 549. OCF₃ OCH₃ H n-C₃H₇ 550. OCF₃ Cl H n-C₃H₇ 551. OCF₃ F H n-C₃H₇ 552. OCF₃ CH₃ H n-C₃H₇ 553. OCF₃ C₂H₅ H n-C₃H₇ 554. OCF₃ CF₃ H n-C₃H₇ 555. OCF₃ OCF₃ H n-C₃H₇ 556. OCF₃ OCHF₂ H n-C₃H₇ 557. OCF₃ Br H CH(CH₃)₂ 558. OCF₃ OCH₃ H CH(CH₃)₂ 559. OCF₃ Cl H CH(CH₃)₂ 560. OCF₃ F H CH(CH₃)₂ 561. OCF₃ CH₃ H CH(CH₃)₂ 562. OCF₃ C₂H₅ H CH(CH₃)₂ 563. OCF₃ CF₃ H CH(CH₃)₂ 564. OCF₃ OCF₃ H CH(CH₃)₂ 565. OCF₃ OCHF₂ H CH(CH₃)₂ 566. OCF₃ Br H n-C₄H₉ 567. OCF₃ OCH₃ H n-C₄H₉ 568. OCF₃ Cl H n-C₄H₉ 569. OCF₃ F H n-C₄H₉ 570. OCF₃ CH₃ H n-C₄H₉ 571. OCF₃ C₂H₅ H n-C₄H₉ 572. OCF₃ CF₃ H n-C₄H₉ 573. OCF₃ OCF₃ H n-C₄H₉ 574. OCF₃ OCHF₂ H n-C₄H₉ 575. OCF₃ Br H C(CH₃)₃ 576. OCF₃ OCH₃ H C(CH₃)₃ 577. OCF₃ Cl H C(CH₃)₃ 578. OCF₃ F H C(CH₃)₃ 579. OCF₃ CH₃ H C(CH₃)₃ 580. OCF₃ C₂H₅ H C(CH₃)₃ 581. OCF₃ CF₃ H C(CH₃)₃ 582. OCF₃ OCF₃ H C(CH₃)₃ 583. OCF₃ OCHF₂ H C(CH₃)₃ 584. OCF₃ Br H C₆H₅ 585. OCF₃ OCH₃ H C₆H₅ 586. OCF₃ Cl H C₆H₅ 587. OCF₃ F H C₆H₅ 588. OCF₃ CH₃ H C₆H₅ 589. OCF₃ C₂H₅ H C₆H₅ 590. OCF₃ CF₃ H C₆H₅ 591. OCF₃ OCF₃ H C₆H₅ 592. OCF₃ OCHF₂ H C₆H₅ 593. OCF₃ Br H cyclopropyl 594. OCF₃ OCH₃ H cyclopropyl 595. OCF₃ Cl H cyclopropyl 596. OCF₃ F H cyclopropyl 597. OCF₃ CH₃ H cyclopropyl 598. OCF₃ C₂H₅ H cyclopropyl 599. OCF₃ CF₃ H cyclopropyl 600. OCF₃ OCF₃ H cyclopropyl 601. OCF₃ OCHF₂ H cyclopropyl 602. OCF₃ Br H CH₂-cyclopropyl 603. OCF₃ OCH₃ H CH₂-cyclopropyl 604. OCF₃ Cl H CH₂-cyclopropyl 605. OCF₃ F H CH₂-cyclopropyl 606. OCF₃ CH₃ H CH₂-cyclopropyl 607. OCF₃ C₂H₅ H CH₂-cyclopropyl 608. OCF₃ OCF₃ H CH₂-cyclopropyl 609. OCF₃ CF₃ H CH₂-cyclopropyl 610. OCF₃ OCHF₂ H CH₂-cyclopropyl 611. OCF₃ Br H cyclobutyl 612. OCF₃ OCH₃ H cyclobutyl 613. OCF₃ Cl H cyclobutyl 614. OCF₃ F H cyclobutyl 615. OCF₃ CH₃ H cyclobutyl 616. OCF₃ C₂H₅ H cyclobutyl 617. OCF₃ QCF₃ H cyclobutyl 618. OCF₃ CF₃ H cyclobutyl 619. OCF₃ OCHF₂ H cyclobutyl 620. OCF₃ Br H cyclopentyl 621. OCF₃ OCH₃ H cyclopentyl 622. OCF₃ Cl H cyclopentyl 623. OCF₃ F H cyclopentyl 624. OCF₃ CH₃ H cyclopentyl 625. OCF₃ C₂H₅ H cyclopentyl 626. OCF₃ OCF₃ H cyclopentyl 627. OCF₃ CF₃ H cyclopentyl 628. OCF₃ OCHF₂ H cyclopentyl 629. OCF₃ Br H cyclohexyl 630. OCF₃ OCH₃ H cyclohexyl 631. OCF₃ Cl H cyclohexyl 632. OCF₃ F H cyclohexyl 633. OCF₃ CH₃ H cyclohexyl 634. OCF₃ C₂H₅ H cyclohexyl 635. OCF₃ OCF₃ H cyclohexyl 636. OCF₃ CF₃ H cyclohexyl 637. OCF₃ OCHF₂ H cyclohexyl 638. OCF₃ H Br H 639. OCF₃ H OCH₃ H 640. OCF₃ H Cl H 641. OCF₃ H F H 642. OCF₃ H CH₃ H 643. OCF₃ H C₂H₅ H 644. OCF₃ H CF₃ H 645. OCF₃ H OCF₃ H 646. OCF₃ H OCHF₂ H 647. OCF₃ H Br CH₃ 648. OCF₃ H OCH₃ CH₃ 649. OCF₃ H Cl CH₃ 650. OCF₃ H F CH₃ 651. OCF₃ H CH₃ CH₃ 652. OCF₃ H C₂H₅ CH₃ 653. OCF₃ H CF₃ CH₃ 654. OCF₃ H OCF₃ CH₃ 655. OCF₃ H OCHF₂ CH₃ 656. OCF₃ H Br C₂H₅ 657. OCF₃ H OCH₃ C₂H₅ 658. OCF₃ H Cl C₂H₅ 659. OCF₃ H F C₂H₅ 660. OCF₃ H CH₃ C₂H₅ 661. OCF₃ H C₂H₅ C₂H₅ 662. OCF₃ H CF₃ C₂H₅ 663. OCF₃ H OCF₃ C₂H₅ 664. OCF₃ H OCHF₂ C₂H₅ 665. OCF₃ H Br n-C₃H₇ 666. OCF₃ H OCH₃ n-C₃H₇ 667. OCF₃ H Cl n-C₃H₇ 668. OCF₃ H F n-C₃H₇ 669. OCF₃ H CH₃ n-C₃H₇ 670. OCF₃ H C₂H₅ n-C₃H₇ 671. OCF₃ H CF₃ n-C₃H₇ 672. OCF₃ H OCF₃ n-C₃H₇ 673. OCF₃ H OCHF₂ n-C₃H₇ 674. OCF₃ H Br CH(CH₃)₂ 675. OCF₃ H OCH₃ CH(CH₃)₂ 676. OCF₃ H Cl CH(CH₃)₂ 677. OCF₃ H F CH(CH₃)₂ 678. OCF₃ H CH₃ CH(CH₃)₂ 679. OCF₃ H C₂H₅ CH(CH₃)₂ 680. OCF₃ H CF₃ CH(CH₃)₂ 681. OCF₃ H OCF₃ CH(CH₃)₂ 682. OCF₃ H OCHF₂ CH(CH₃)₂ 683. OCF₃ H Br n-C₄H₉ 684. OCF₃ H OCH₃ n-C₄H₉ 685. OCF₃ H Cl n-C₄H₉ 686. OCF₃ H F n-C₄H₉ 687. OCF₃ H CH₃ n-C₄H₉ 688. OCF₃ H C₂H₅ n-C₄H₉ 689. OCF₃ H CF₃ n-C₄H₉ 690. OCF₃ H OCF₃ n-C₄H₉ 691. OCF₃ H OCHF₂ n-C₄H₉ 692. OCF₃ H Br C(CH₃)₃ 693. OCF₃ H OCH₃ C(CH₃)₃ 694. OCF₃ H Cl C(CH₃)₃ 695. OCF₃ H F C(CH₃)₃ 696. OCF₃ H CH₃ C(CH₃)₃ 697. OCF₃ H C₂H₅ C(CH₃)₃ 698. OCF₃ H CF₃ C(CH₃)₃ 699. OCF₃ H OCF₃ C(CH₃)₃ 700. OCF₃ H OCHF₂ C(CH₃)₃ 701. OCF₃ H Br C₆H₅ 702. OCF₃ H OCH₃ C₆H₅ 703. OCF₃ H Cl C₆H₅ 704. OCF₃ H F C₆H₅ 705. OCF₃ H CH₃ C₆H₅ 706. OCF₃ H C₂H₅ C₆H₅ 707. OCF₃ H CF₃ C₆H₅ 708. OCF₃ H OCF₃ C₆H₅ 709. OCF₃ H OCHF₂ C₆H₅ 710. OCF₃ H Br cyclopropyl 711. OCF₃ H OCH₃ cyclopropyl 712. OCF₃ H Cl cyclopropyl 713. OCF₃ H F cyclopropyl 714. OCF₃ H CH₃ cyclopropyl 715. OCF₃ H C₂H₅ cyclopropyl 716. OCF₃ H CF₃ cyclopropyl 717. OCF₃ H OCF₃ cyclopropyl 718. OCF₃ H OCHF₂ cyclopropyl 719. OCF₃ H Br CH₂-cyclopropyl 720. OCF₃ H OCH₃ CH₂-cyclopropyl 721. OCF₃ H Cl CH₂-cyclopropyl 722. OCF₃ H F CH₂-cyclopropyl 723. OCF₃ H CH₃ CH₂-cyclopropyl 724. OCF₃ H C₂H₅ CH₂-cyclopropyl 725. OCF₃ H CF₃ CH₂-cyclopropyl 726. OCF₃ H OCF₃ CH₂-cyclopropyl 727. OCF₃ H OCHF₂ CH₂-cyclopropyl 728. OCF₃ H Br cyclobutyl 729. OCF₃ H OCH₃ cyclobutyl 730. OCF₃ H Cl cyclobutyl 731. OCF₃ H F cyclobutyl 732. OCF₃ H CH₃ cyclobutyl 733. OCF₃ H C₂H₅ cyclobutyl 734. OCF₃ H CF₃ cyclobutyl 735. OCF₃ H OCF₃ cyclobutyl 736. OCF₃ H OCHF₂ cyclobutyl 737. OCF₃ H Br cyclopentyl 738. OCF₃ H OCH₃ cyclopentyl 739. OCF₃ H Cl cyclopentyl 740. OCF₃ H F cyclopentyl 741. OCF₃ H CH₃ cyclopentyl 742. OCF₃ H C₂H₅ cyclopentyl 743. OCF₃ H CF₃ cyclopentyl 744. OCF₃ H OCF₃ cyclopentyl 745. OCF₃ H OCHF₂ cyclopentyl 746. OCF₃ H Br cyclohexyl 747. OCF₃ H OCH₃ cyclohexyl 748. OCF₃ H Cl cyclohexyl 749. OCF₃ H F cyclohexyl 750. OCF₃ H CH₃ cyclohexyl 751. OCF₃ H C₂H₅ cyclohexyl 752. OCF₃ H CF₃ cyclohexyl 753. OCF₃ H OCF₃ cyclohexyl 754. OCF₃ H OCHF₂ cyclohexyl 755. OCHF₂ Br H H 756. OCHF₂ OCH₃ H H 757. OCHF₂ Cl H H 758. OCHF₂ F H H 759. OCHF₂ CH₃ H H 760. OCHF₂ C₂H₅ H H 761. OCHF₂ OCF₃ H H 762. OCHF₂ CF₃ H H 763. OCHF₂ Br H CH₃ 764. OCHF₂ OCH₃ H CH₃ 765. OCHF₂ Cl H CH₃ 766. OCHF₂ F H CH₃ 767. OCHF₂ CH₃ H CH₃ 768. OCHF₂ C₂H₅ H CH₃ 769. OCHF₂ OCF₃ H CH₃ 770. OCHF₂ CF₃ H CH₃ 771. OCHF₂ Br H C₂H₅ 772. OCHF₂ OCH₃ H C₂H₅ 773. OCHF₂ Cl H C₂H₅ 774. OCHF₂ F H C₂H₅ 775. OCHF₂ CH₃ H C₂H₅ 776. OCHF₂ C₂H₅ H C₂H₅ 777. OCHF₂ OCF₃ H C₂H₅ 778. OCHF₂ CF₃ H C₂H₅ 779. OCHF₂ Br H n-C₃H₇ 780. OCHF₂ OCH₃ H n-C₃H₇ 781. OCHF₂ Cl H n-C₃H₇ 782. OCHF₂ F H n-C₃H₇ 783. OCHF₂ CH₃ H n-C₃H₇ 784. OCHF₂ C₂H₅ H n-C₃H₇ 785. OCHF₂ OCF₃ H n-C₃H₇ 786. OCHF₂ CF₃ H n-C₃H₇ 787. OCHF₂ Br H CH(CH₃)₂ 788. OCHF₂ OCH₃ H CH(CH₃)₂ 789. OCHF₂ Cl H CH(CH₃)₂ 790. OCHF₂ F H CH(CH₃)₂ 791. OCHF₂ CH₃ H CH(CH₃)₂ 792. OCHF₂ C₂H₅ H CH(CH₃)₂ 793. OCHF₂ OCF₃ H CH(CH₃)₂ 794. OCHF₂ CF₃ H CH(CH₃)₂ 795. OCHF₂ Br H n-C₄H₉ 796. OCHF₂ OCH₃ H n-C₄H₉ 797. OCHF₂ Cl H n-C₄H₉ 798. OCHF₂ F H n-C₄H₉ 799. OCHF₂ CH₃ H n-C₄H₉ 800. OCHF₂ C₂H₅ H n-C₄H₉ 801. OCHF₂ OCF₃ H n-C₄H₉ 802. OCHF₂ CF₃ H n-C₄H₉ 803. OCHF₂ Br H C(CH₃)₃ 804. OCHF₂ OCH₃ H C(CH₃)₃ 805. OCHF₂ Cl H C(CH₃)₃ 806. OCHF₂ F H C(CH₃)₃ 807. OCHF₂ CH₃ H C(CH₃)₃ 808. OCHF₂ C₂H₅ H C(CH₃)₃ 809. OCHF₂ OCF₃ H C(CH₃)₃ 810. OCHF₂ CF₃ H C(CH₃)₃ 811. OCHF₂ Br H C₆H₅ 812. OCHF₂ OCH₃ H C₆H₅ 813. OCHF₂ Cl H C₆H₅ 814. OCHF₂ F H C₆H₅ 815. OCHF₂ CH₃ H C₆H₅ 816. OCHF₂ C₂H₅ H C₆H₅ 817. OCHF₂ OCF₃ H C₆H₅ 818. OCHF₂ CF₃ H C₆H₅ 819. OCHF₂ Br H cyclopropyl 820. OCHF₂ OCH₃ H cyclopropyl 821. OCHF₂ Cl H cyclopropyl 822. OCHF₂ F H cyclopropyl 823. OCHF₂ CH₃ H cyclopropyl 824. OCHF₂ C₂H₅ H cyclopropyl 825. OCHF₂ OCF₃ H cyclopropyl 826. OCHF₂ CF₃ H cyclopropyl 827. OCHF₂ Br H CH₂-cyclopropyl 828. OCHF₂ OCH₃ H CH₂-cyclopropyl 829. OCHF₂ Cl H CH₂-cyclopropyl 830. OCHF₂ F H CH₂-cyclopropyl 831. OCHF₂ CH₃ H CH₂-cyclopropyl 832. OCHF₂ C₂H₅ H CH₂-cyclopropyl 833. OCHF₂ OCF₃ H CH₂-cyclopropyl 834. OCHF₂ CF₃ H CH₂-cyclopropyl 835. OCHF₂ Br H cyclobutyl 836. OCHF₂ OCH₃ H cyclobutyl 837. OCHF₂ Cl H cyclobutyl 838. OCHF₂ F H cyclobutyl 839. OCHF₂ CH₃ H cyclobutyl 840. OCHF₂ C₂H₅ H cyclobutyl 841. OCHF₂ OCF₃ H cyclobutyl 842. OCHF₂ CF₃ H cyclobutyl 843. OCHF₂ Br H cyclopentyl 844. OCHF₂ OCH₃ H cyclopentyl 845. OCHF₂ Cl H cyclopentyl 846. OCHF₂ F H cyclopentyl 847. OCHF₂ CH₃ H cyclopentyl 848. OCHF₂ C₂H₅ H cyclopentyl 849. OCHF₂ OCF₃ H cyclopentyl 850. OCHF₂ CF₃ H cyclopentyl 851. OCHF₂ Br H cyclohexyl 852. OCHF₂ OCH₃ H cyclohexyl 853. OCHF₂ Cl H cyclohexyl 854. OCHF₂ F H cyclohexyl 855. OCHF₂ CH₃ H cyclohexyl 856. OCHF₂ C₂H₅ H cyclohexyl 857. OCHF₂ OCF₃ H cyclohexyl 858. OCHF₂ CF₃ H cyclohexyl 859. OCHF₂ H Br H 860. OCHF₂ H OCH₃ H 861. OCHF₂ H Cl H 862. OCHF₂ H F H 863. OCHF₂ H CH₃ H 864. OCHF₂ H C₂H₅ H 865. OCHF₂ H OCF₃ H 866. OCHF₂ H CF₃ H 867. OCHF₂ H Br CH₃ 868. OCHF₂ H OCH₃ CH₃ 869. OCHF₂ H Cl CH₃ 870. OCHF₂ H F CH₃ 871. OCHF₂ H CH₃ CH₃ 872. OCHF₂ H C₂H₅ CH₃ 873. OCHF₂ H OCF₃ CH₃ 874. OCHF₂ H CF₃ CH₃ 875. OCHF₂ H Br C₂H₅ 876. OCHF₂ H OCH₃ C₂H₅ 877. OCHF₂ H Cl C₂H₅ 878. OCHF₂ H F C₂H₅ 879. OCHF₂ H CH₃ C₂H₅ 880. OCHF₂ H C₂H₅ C₂H₅ 881. OCHF₂ H OCF₃ C₂H₅ 882. OCHF₂ H CF₃ C₂H₅ 883. OCHF₂ H Br n-C₃H₇ 884. OCHF₂ H OCH₃ n-C₃H₇ 885. OCHF₂ H Cl n-C₃H₇ 886. OCHF₂ H F n-C₃H₇ 887. OCHF₂ H CH₃ n-C₃H₇ 888. OCHF₂ H C₂H₅ n-C₃H₇ 889. OCHF₂ H OCF₃ n-C₃H₇ 890. OCHF₂ H CF₃ n-C₃H₇ 891. OCHF₂ H Br CH(CH₃)₂ 892. OCHF₂ H OCH₃ CH(CH₃)₂ 893. OCHF₂ H Cl CH(CH₃)₂ 894. OCHF₂ H F CH(CH₃)₂ 895. OCHF₂ H CH₃ CH(CH₃)₂ 896. OCHF₂ H C₂H₅ CH(CH₃)₂ 897. OCHF₂ H OCF₃ CH(CH₃)₂ 898. OCHF₂ H CF₃ CH(CH₃)₂ 899. OCHF₂ H Br n-C₄H₉ 900. OCHF₂ H OCH₃ n-C₄H₉ 901. OCHF₂ H Cl n-C₄H₉ 902. OCHF₂ H F n-C₄H₉ 903. OCHF₂ H CH₃ n-C₄H₉ 904. OCHF₂ H C₂H₅ n-C₄H₉ 905. OCHF₂ H OCF₃ n-C₄H₉ 906. OCHF₂ H CF₃ n-C₄H₉ 907. OCHF₂ H Br C(CH₃)₃ 908. OCHF₂ H OCH₃ C(CH₃)₃ 909. OCHF₂ H Cl C(CH₃)₃ 910. OCHF₂ H F C(CH₃)₃ 911. OCHF₂ H CH₃ C(CH₃)₃ 912. OCHF₂ H C₂H₅ C(CH₃)₃ 913. OCHF₂ H OCF₃ C(CH₃)₃ 914. OCHF₂ H CF₃ C(CH₃)₃ 915. OCHF₂ H Br C₆H₅ 916. OCHF₂ H OCH₃ C₆H₅ 917. OCHF₂ H Cl C₆H₅ 918. OCHF₂ H F C₆H₅ 919. OCHF₂ H CH₃ C₆H₅ 920. OCHF₂ H C₂H₅ C₆H₅ 921. OCHF₂ H OCF₃ C₆H₅ 922. OCHF₂ H CF₃ C₆H₅ 923. OCHF₂ H Br cyclopropyl 924. OCHF₂ H OCH₃ cyclopropyl 925. OCHF₂ H Cl cyclopropyl 926. OCHF₂ H F cyclopropyl 927. OCHF₂ H CH₃ cyclopropyl 928. OCHF₂ H C₂H₅ cyclopropyl 929. OCHF₂ H OCF₃ cyclopropyl 930. OCHF₂ H CF₃ cyclopropyl 931. OCHF₂ H Br CH₂-cyclopropyl 932. OCHF₂ H OCH₃ CH₂-cyclopropyl 933. OCHF₂ H Cl CH₂-cyclopropyl 934. OCHF₂ H F CH₂-cyclopropyl 935. OCHF₂ H CH₃ CH₂-cyclopropyl 936. OCHF₂ H C₂H₅ CH₂-cyclopropyl 937. OCHF₂ H OCF₃ CH₂-cyclopropyl 938. OCHF₂ H CF₃ CH₂-cyclopropyl 939. OCHF₂ H Br cyclobutyl 940. OCHF₂ H OCH₃ cyclobutyl 941. OCHF₂ H Cl cyclobutyl 942. OCHF₂ H F cyclobutyl 943. OCHF₂ H CH₃ cyclobutyl 944. OCHF₂ H C₂H₅ cyclobutyl 945. OCHF₂ H OCF₃ cyclobutyl 946. OCHF₂ H CF₃ cyclobutyl 947. OCHF₂ H Br cyclopentyl 948. OCHF₂ H OCH₃ cyclopentyl 949. OCHF₂ H Cl cyclopentyl 950. OCHF₂ H F cyclopentyl 951. OCHF₂ H CH₃ cyclopentyl 952. OCHF₂ H C₂H₅ cyclopentyl 953. OCHF₂ H OCF₃ cyclopentyl 954. OCHF₂ H CF₃ cyclopentyl 955. OCHF₂ H Br cyclohexyl 956. OCHF₂ H OCH₃ cyclohexyl 957. OCHF₂ H Cl cyclohexyl 958. OCHF₂ H F cyclohexyl 959. OCHF₂ H CH₃ cyclohexyl 960. OCHF₂ H C₂H₅ cyclohexyl 961. OCHF₂ H OCF₃ cyclohexyl 962. OCHF₂ H CF₃ cyclohexyl 963. OCH₃ Br H H 964. OCH₃ OCH₃ H H 965. OCH₃ Cl H H 966. OCH₃ F H H 967. OCH₃ CH₃ H H 968. OCH₃ C₂H₅ H H 969. OCH₃ CF₃ H H 970. OCH₃ OCF₃ H H 971. OCH₃ OCHF₂ H H 972. OCH₃ Br H CH₃ 973. OCH₃ OCH₃ H CH₃ 974. OCH₃ Cl H CH₃ 975. OCH₃ F H CH₃ 976. OCH₃ CH₃ H CH₃ 977. OCH₃ C₂H₅ H CH₃ 978. OCH₃ CF₃ H CH₃ 979. OCH₃ OCF₃ H CH₃ 980. OCH₃ OCHF₂ H CH₃ 981. OCH₃ Br H C₂H₅ 982. OCH₃ OCH₃ H C₂H₅ 983. OCH₃ Cl H C₂H₅ 984. OCH₃ F H C₂H₅ 985. OCH₃ CH₃ H C₂H₅ 986. OCH₃ C₂H₅ H C₂H₅ 987. OCH₃ CF₃ H C₂H₅ 988. OCH₃ OCF₃ H C₂H₅ 989. OCH₃ OCHF₂ H C₂H₅ 990. OCH₃ Br H n-C₃H₇ 991. OCH₃ OCH₃ H n-C₃H₇ 992. OCH₃ Cl H n-C₃H₇ 993. OCH₃ F H n-C₃H₇ 994. OCH₃ CH₃ H n-C₃H₇ 995. OCH₃ C₂H₅ H n-C₃H₇ 996. OCH₃ CF₃ H n-C₃H₇ 997. OCH₃ OCF₃ H n-C₃H₇ 998. OCH₃ OCHF₂ H n-C₃H₇ 999. OCH₃ Br H CH(CH₃)₂ 1000. OCH₃ OCH₃ H CH(CH₃)₂ 1001. OCH₃ Cl H CH(CH₃)₂ 1002. OCH₃ F H CH(CH₃)₂ 1003. OCH₃ CH₃ H CH(CH₃)₂ 1004. OCH₃ C₂H₅ H CH(CH₃)₂ 1005. OCH₃ CF₃ H CH(CH₃)₂ 1006. OCH₃ OCF₃ H CH(CH₃)₂ 1007. OCH₃ OCHF₂ H CH(CH₃)₂ 1008. OCH₃ Br H n-C₄H₉ 1009. OCH₃ OCH₃ H n-C₄H₉ 1010. OCH₃ Cl H n-C₄H₉ 1011. OCH₃ F H n-C₄H₉ 1012. OCH₃ CH₃ H n-C₄H₉ 1013. OCH₃ C₂H₅ H n-C₄H₉ 1014. OCH₃ CF₃ H n-C₄H₉ 1015. OCH₃ OCF₃ H n-C₄H₉ 1016. OCH₃ OCHF₂ H n-C₄H₉ 1017. OCH₃ Br H C(CH₃)₃ 1018. OCH₃ OCH₃ H C(CH₃)₃ 1019. OCH₃ Cl H C(CH₃)₃ 1020. OCH₃ F H C(CH₃)₃ 1021. OCH₃ CH₃ H C(CH₃)₃ 1022. OCH₃ C₂H₅ H C(CH₃)₃ 1023. OCH₃ CF₃ H C(CH₃)₃ 1024. OCH₃ OCF₃ H C(CH₃)₃ 1025. OCH₃ OCHF₂ H C(CH₃)₃ 1026. OCH₃ Br H C₆H₅ 1027. OCH₃ OCH₃ H C₆H₅ 1028. OCH₃ Cl H C₆H₅ 1029. OCH₃ F H C₆H₅ 1030. OCH₃ CH₃ H C₆H₅ 1031. OCH₃ C₂H₅ H C₆H₅ 1032. OCH₃ CF₃ H C₆H₅ 1033. OCH₃ OCF₃ H C₆H₅ 1034. OCH₃ OCHF₂ H C₆H₅ 1035. OCH₃ Br H cyclopropyl 1036. OCH₃ OCH₃ H cyclopropyl 1037. OCH₃ Cl H cyclopropyl 1038. OCH₃ F H cyclopropyl 1039. OCH₃ CH₃ H cyclopropyl 1040. OCH₃ C₂H₅ H cyclopropyl 1041. OCH₃ CF₃ H cyclopropyl 1042. OCH₃ OCF₃ H cyclopropyl 1043. OCH₃ OCHF₂ H cyclopropyl 1044. OCH₃ Br H CH₂-cyclopropyl 1045. OCH₃ OCH₃ H CH₂-cyclopropyl 1046. OCH₃ Cl H CH₂-cyclopropyl 1047. OCH₃ F H CH₂-cyclopropyl 1048. OCH₃ CH₃ H CH₂-cyclopropyl 1049. OCH₃ C₂H₅ H CH₂-cyclopropyl 1050. OCH₃ CF₃ H CH₂-cyclopropyl 1051. OCH₃ OCF₃ H CH₂-cyclopropyl 1052. OCH₃ OCHF₂ H CH₂-cyclopropyl 1053. OCH₃ Br H cyclobutyl 1054. OCH₃ OCH₃ H cyclobutyl 1055. OCH₃ Cl H cyclobutyl 1056. OCH₃ F H cyclobutyl 1057. OCH₃ CH₃ H cyclobutyl 1058. OCH₃ C₂H₅ H cyclobutyl 1059. OCH₃ CF₃ H cyclobutyl 1060. OCH₃ OCF₃ H cyclobutyl 1061. OCH₃ OCHF₂ H cyclobutyl 1062. OCH₃ Br H cyclopentyl 1063. OCH₃ OCH₃ H cyclopentyl 1064. OCH₃ Cl H cyclopentyl 1065. OCH₃ F H cyclopentyl 1066. OCH₃ CH₃ H cyclopentyl 1067. OCH₃ C₂H₅ H cyclopentyl 1068. OCH₃ CF₃ H cyclopentyl 1069. OCH₃ OCF₃ H cyclopentyl 1070. OCH₃ OCHF₂ H cyclopentyl 1071. OCH₃ Br H cyclohexyl 1072. OCH₃ OCH₃ H cyclohexyl 1073. OCH₃ Cl H cyclohexyl 1074. OCH₃ F H cyclohexyl 1075. OCH₃ CH₃ H cyclohexyl 1076. OCH₃ C₂H₅ H cyclohexyl 1077. OCH₃ CF₃ H cyclohexyl 1078. OCH₃ OCF₃ H cyclohexyl 1079. OCH₃ OCHF₂ H cyclohexyl 1080. OCH₃ H Br H 1081. OCH₃ H OCH₃ H 1082. OCH₃ H Cl H 1083. OCH₃ H F H 1084. OCH₃ H CH₃ H 1085. OCH₃ H C₂H₅ H 1086. OCH₃ H CF₃ H 1087. OCH₃ H OCF₃ H 1088. OCH₃ H OCHF₂ H 1089. OCH₃ H Br CH₃ 1090. OCH₃ H OCH₃ CH₃ 1091. OCH₃ H Cl CH₃ 1092. OCH₃ H F CH₃ 1093. OCH₃ H CH₃ CH₃ 1094. OCH₃ H C₂H₅ CH₃ 1095. OCH₃ H CF₃ CH₃ 1096. OCH₃ H OCF₃ CH₃ 1097. OCH₃ H OCHF₂ CH₃ 1098. OCH₃ H Br C₂H₅ 1099. OCH₃ H OCH₃ C₂H₅ 1100. OCH₃ H Cl C₂H₅ 1101. OCH₃ H F C₂H₅ 1102. OCH₃ H CH₃ C₂H₅ 1103. OCH₃ H C₂H₅ C₂H₅ 1104. OCH₃ H CF₃ C₂H₅ 1105. OCH₃ H OCF₃ C₂H₅ 1106. OCH₃ H OCHF₂ C₂H₅ 1107. OCH₃ H Br n-C₃H₇ 1108. OCH₃ H OCH₃ n-C₃H₇ 1109. OCH₃ H Cl n-C₃H₇ 1110. OCH₃ H F n-C₃H₇ 1111. OCH₃ H CH₃ n-C₃H₇ 1112. OCH₃ H C₂H₅ n-C₃H₇ 1113. OCH₃ H CF₃ n-C₃H₇ 1114. OCH₃ H OCF₃ n-C₃H₇ 1115. OCH₃ H OCHF₂ n-C₃H₇ 1116. OCH₃ H Br CH(CH₃)₂ 1117. OCH₃ H OCH₃ CH(CH₃)₂ 1118. OCH₃ H Cl CH(CH₃)₂ 1119. OCH₃ H F CH(CH₃)₂ 1120. OCH₃ H CH₃ CH(CH₃)₂ 1121. OCH₃ H C₂H₅ CH(CH₃)₂ 1122. OCH₃ H CF₃ CH(CH₃)₂ 1123. OCH₃ H OCF₃ CH(CH₃)₂ 1124. OCH₃ H OCHF₂ CH(CH₃)₂ 1125. OCH₃ H Br n-C₄H₉ 1126. OCH₃ H OCH₃ n-C₄H₉ 1127. OCH₃ H Cl n-C₄H₉ 1128. OCH₃ H F n-C₄H₉ 1129. OCH₃ H CH₃ n-C₄H₉ 1130. OCH₃ H C₂H₅ n-C₄H₉ 1131. OCH₃ H CF₃ n-C₄H₉ 1132. OCH₃ H OCF₃ n-C₄H₉ 1133. OCH₃ H OCHF₂ n-C₄H₉ 1134. OCH₃ H Br C(CH₃)₃ 1135. OCH₃ H OCH₃ C(CH₃)₃ 1136. OCH₃ H Cl C(CH₃)₃ 1137. OCH₃ H F C(CH₃)₃ 1138. OCH₃ H CH₃ C(CH₃)₃ 1139. OCH₃ H C₂H₅ C(CH₃)₃ 1140. OCH₃ H CF₃ C(CH₃)₃ 1141. OCH₃ H OCF₃ C(CH₃)₃ 1142. OCH₃ H OCHF₂ C(CH₃)₃ 1143. OCH₃ H Br C₆H₅ 1144. OCH₃ H OCH₃ C₆H₅ 1145. OCH₃ H Cl C₆H₅ 1146. OCH₃ H F C₆H₅ 1147. OCH₃ H CH₃ C₆H₅ 1148. OCH₃ H C₂H₅ C₆H₅ 1149. OCH₃ H CF₃ C₆H₅ 1150. OCH₃ H OCF₃ C₆H₅ 1151. OCH₃ H OCHF₂ C₆H₅ 1152. OCH₃ H Br cyclopropyl 1153. OCH₃ H OCH₃ cyclopropyl 1154. OCH₃ H Cl cyclopropyl 1155. OCH₃ H F cyclopropyl 1156. OCH₃ H CH₃ cyclopropyl 1157. OCH₃ H C₂H₅ cyclopropyl 1158. OCH₃ H CF₃ cyclopropyl 1159. OCH₃ H OCF₃ cyclopropyl 1160. OCH₃ H OCHF₂ cyclopropyl 1161. OCH₃ H Br CH₂-cyclopropyl 1162. OCH₃ H OCH₃ CH₂-cyclopropyl 1163. OCH₃ H Cl CH₂-cyclopropyl 1164. OCH₃ H F CH₂-cyclopropyl 1165. OCH₃ H CH₃ CH₂-cyclopropyl 1166. OCH₃ H C₂H₅ CH₂-cyclopropyl 1167. OCH₃ H CF₃ CH₂-cyclopropyl 1168. OCH₃ H OCF₃ CH₂-cyclopropyl 1169. OCH₃ H OCHF₂ CH₂-cyclopropyl 1170. OCH₃ H Br cyclobutyl 1171. OCH₃ H OCH₃ cyclobutyl 1172. OCH₃ H Cl cyclobutyl 1173. OCH₃ H F cyclobutyl 1174. OCH₃ H CH₃ cyclobutyl 1175. OCH₃ H C₂H₅ cyclobutyl 1176. OCH₃ H CF₃ cyclobutyl 1177. OCH₃ H OCF₃ cyclobutyl 1178. OCH₃ H OCHF₂ cyclobutyl 1179. OCH₃ H Br cyclopentyl 1180. OCH₃ H OCH₃ cyclopentyl 1181. OCH₃ H Cl cyclopentyl 1182. OCH₃ H F cyclopentyl 1183. OCH₃ H CH₃ cyclopentyl 1184. OCH₃ H C₂H₅ cyclopentyl 1185. OCH₃ H CF₃ cyclopentyl 1186. OCH₃ H OCF₃ cyclopentyl 1187. OCH₃ H OCHF₂ cyclopentyl 1188. OCH₃ H Br cyclohexyl 1189. OCH₃ H OCH₃ cyclohexyl 1190. OCH₃ H Cl cyclohexyl 1191. OCH₃ H F cyclohexyl 1192. OCH₃ H CH₃ cyclohexyl 1193. OCH₃ H C₂H₅ cyclohexyl 1194. OCH₃ H CF₃ cyclohexyl 1195. OCH₃ H OCF₃ cyclohexyl 1196. OCH₃ H OCHF₂ cyclohexyl 1197. Cl Cl H H 1198. Cl F H H 1199. Cl CH₃ H H 1200. Cl OCH₃ H H 1201. Cl Br H H 1202. Cl CF₃ H H 1203. Cl OCF₃ H H 1204. Cl Cl H CH₃ 1205. Cl F H CH₃ 1206. Cl CH₃ H CH₃ 1207. Cl OCH₃ H CH₃ 1208. Cl Br H CH₃ 1209. Cl CF₃ H CH₃ 1210. Cl OCF₃ H CH₃ 1211. Cl Cl H C₂H₅ 1212. Cl F H C₂H₅ 1213. Cl CH₃ H C₂H₅ 1214. Cl OCH₃ H C₂H₅ 1215. Cl Br H C₂H₅ 1216. Cl CF₃ H C₂H₅ 1217. Cl OCF₃ H C₂H₅ 1218. Cl Cl H n-C₃H₇ 1219. Cl F H n-C₃H₇ 1220. Cl CH₃ H n-C₃H₇ 1221. Cl OCH₃ H n-C₃H₇ 1222. Cl Br H n-C₃H₇ 1223. Cl CF₃ H n-C₃H₇ 1224. Cl OCF₃ H n-C₃H₇ 1225. Cl Cl H CH(CH₃)₂ 1226. Cl F H CH(CH₃)₂ 1227. Cl CH₃ H CH(CH₃)₂ 1228. Cl OCH₃ H CH(CH₃)₂ 1229. Cl Br H CH(CH₃)₂ 1230. Cl CF₃ H CH(CH₃)₂ 1231. Cl OCF₃ H CH(CH₃)₂ 1232. Cl Cl H n-C₄H₉ 1233. Cl F H n-C₄H₉ 1234. Cl CH₃ H n-C₄H₉ 1235. Cl OCH₃ H n-C₄H₉ 1236. Cl Br H n-C₄H₉ 1237. Cl CF₃ H n-C₄H₉ 1238. Cl OCF₃ H n-C₄H₉ 1239. Cl Cl H C(CH₃)₃ 1240. Cl F H C(CH₃)₃ 1241. Cl CH₃ H C(CH₃)₃ 1242. Cl OCH₃ H C(CH₃)₃ 1243. Cl Br H C(CH₃)₃ 1244. Cl CF₃ H C(CH₃)₃ 1245. Cl OCF₃ H C(CH₃)₃ 1246. Cl Cl H C₆H₅ 1247. Cl F H C₆H₅ 1248. Cl CH₃ H C₆H₅ 1249. Cl OCH₃ H C₆H₅ 1250. Cl Br H C₆H₅ 1251. Cl CF₃ H C₆H₅ 1252. Cl OCF₃ H C₆H₅ 1253. Cl Cl H cyclopropyl 1254. Cl F H cyclopropyl 1255. Cl CH₃ H cyclopropyl 1256. Cl OCH₃ H cyclopropyl 1257. Cl Br H cyclopropyl 1258. Cl CF₃ H cyclopropyl 1259. Cl OCF₃ H cyclopropyl 1260. Cl Cl H CH₂-cyclopropyl 1261. Cl F H CH₂-cyclopropyl 1262. Cl CH₃ H CH₂-cyclopropyl 1263. Cl OCH₃ H CH₂-cyclopropyl 1264. Cl Br H CH₂-cyclopropyl 1265. Cl CF₃ H CH₂-cyclopropyl 1266. Cl OCF₃ H CH₂-cyclopropyl 1267. Cl Cl H cyclobutyl 1268. Cl F H cyclobutyl 1269. Cl CH₃ H cyclobutyl 1270. Cl OCH₃ H cyclobutyl 1271. Cl Br H cyclobutyl 1272. Cl CF₃ H cyclobutyl 1273. Cl OCF₃ H cyclobutyl 1274. Cl Cl H cyclopentyl 1275. Cl F H cyclopentyl 1276. Cl CH₃ H cyclopentyl 1277. Cl OCH₃ H cyclopentyl 1278. Cl Br H cyclopentyl 1279. Cl CF₃ H cyclopentyl 1280. Cl OCF₃ H cyclopentyl 1281. Cl Cl H cyclohexyl 1282. Cl F H cyclohexyl 1283. Cl CH₃ H cyclohexyl 1284. Cl OCH₃ H cyclohexyl 1285. Cl Br H cyclohexyl 1286. Cl CF₃ H cyclohexyl 1287. Cl OCF₃ H cyclohexyl 1288. Cl H Cl H 1289. Cl H F H 1290. Cl H CH₃ H 1291. Cl H OCH₃ H 1292. Cl H Br H 1293. Cl H CF₃ H 1294. Cl H OCF₃ H 1295. Cl H Cl CH₃ 1296. Cl H F CH₃ 1297. Cl H CH₃ CH₃ 1298. Cl H OCH₃ CH₃ 1299. Cl H Br CH₃ 1300. Cl H CF₃ CH₃ 1301. Cl H OCF₃ CH₃ 1302. Cl H Cl C₂H₅ 1303. Cl H F C₂H₅ 1304. Cl H CH₃ C₂H₅ 1305. Cl H OCH₃ C₂H₅ 1306. Cl H Br C₂H₅ 1307. Cl H CF₃ C₂H₅ 1308. Cl H OCF₃ C₂H₅ 1309. Cl H Cl n-C₃H₇ 1310. Cl H F n-C₃H₇ 1311. Cl H CH₃ n-C₃H₇ 1312. Cl H OCH₃ n-C₃H₇ 1313. Cl H Br n-C₃H₇ 1314. Cl H CF₃ n-C₃H₇ 1315. Cl H OCF₃ n-C₃H₇ 1316. Cl H Cl CH(CH₃)₂ 1317. Cl H F CH(CH₃)₂ 1318. Cl H CH₃ CH(CH₃)₂ 1319. Cl H OCH₃ CH(CH₃)₂ 1320. Cl H Br CH(CH₃)₂ 1321. Cl H CF₃ CH(CH₃)₂ 1322. Cl H OCF₃ CH(CH₃)₂ 1323. Cl H Cl n-C₄H₉ 1324. Cl H F n-C₄H₉ 1325. Cl H CH₃ n-C₄H₉ 1326. Cl H OCH₃ n-C₄H₉ 1327. Cl H Br n-C₄H₉ 1328. Cl H CF₃ n-C₄H₉ 1329. Cl H OCF₃ n-C₄H₉ 1330. Cl H Cl C(CH₃)₃ 1331. Cl H F C(CH₃)₃ 1332. Cl H CH₃ C(CH₃)₃ 1333. Cl H OCH₃ C(CH₃)₃ 1334. Cl H Br C(CH₃)₃ 1335. Cl H CF₃ C(CH₃)₃ 1336. Cl H OCF₃ C(CH₃)₃ 1337. Cl. H Cl C₆H₅ 1338. Cl H F C₆H₅ 1339. Cl H CH₃ C₆H₅ 1340. Cl H OCH₃ C₆H₅ 1341. Cl H Br C₆H₅ 1342. Cl H CF₃ C₆H₅ 1343. Cl H OCF₃ C₆H₅ 1344. Cl H Cl cyclopropyl 1345. Cl H F cyclopropyl 1346. Cl H CH₃ cyclopropyl 1347. Cl H OCH₃ cyclopropyl 1348. Cl H Br cyclopropyl 1349. Cl H CF₃ cyclopropyl 1350. Cl H OCF₃ cyclopropyl 1351. Cl H Cl CH₂-cyclopropyl 1352. Cl H F CH₂-cyclopropyl 1353. Cl H CH₃ CH₂-cyclopropyl 1354. Cl H OCH₃ CH₂-cyclopropyl 1355. Cl H Br CH₂-cyclopropyl 1356. Cl H CF₃ CH₂-cyclopropyl 1357. Cl H OCF₃ CH₂-cyclopropyl 1358. Cl H Cl cyclobutyl 1359. Cl H F cyclobutyl 1360. Cl H CH₃ cyclobutyl 1361. Cl H OCH₃ cyclobutyl 1362. Cl H Br cyclobutyl 1363. Cl H CF₃ cyclobutyl 1364. Cl H OCF₃ cyclobutyl 1365. Cl H Cl cyclopentyl 1366. Cl H F cyclopentyl 1367. Cl H CH₃ cyclopentyl 1368. Cl H OCH₃ cyclopentyl 1369. Cl H Br cyclopentyl 1370. Cl H CF₃ cyclopentyl 1371. Cl H OCF₃ cyclopentyl 1372. Cl H Cl cyclohexyl 1373. Cl H F cyclohexyl 1374. Cl H CH₃ cyclohexyl 1375. Cl H OCH₃ cyclohexyl 1376. Cl H Br cyclohexyl 1377. Cl H CF₃ cyclohexyl 1378. Cl H OCF₃ cyclohexyl 1379. Br Cl H H 1380. Br F H H 1381. Br CH₃ H H 1382. Br OCH₃ H H 1383. Br Br H H 1384. Br CF₃ H H 1385. Br OCF₃ H H 1386. Br Cl H CH₃ 1387. Br F H CH₃ 1388. Br CH₃ H CH₃ 1389. Br OCH₃ H CH₃ 1390. Br Br H CH₃ 1391. Br CF₃ H CH₃ 1392. Br OCF₃ H CH₃ 1393. Br Cl H C₂H₅ 1394. Br F H C₂H₅ 1395. Br CH₃ H C₂H₅ 1396. Br OCH₃ H C₂H₅ 1397. Br Br H C₂H₅ 1398. Br CF₃ H C₂H₅ 1399. Br OCF₃ H C₂H₅ 1400. Br Cl H n-C₃H₇ 1401. Br F H n-C₃H₇ 1402. Br CH₃ H n-C₃H₇ 1403. Br OCH₃ H n-C₃H₇ 1404. Br Br H n-C₃H₇ 1405. Br CF₃ H n-C₃H₇ 1406. Br OCF₃ H n-C₃H₇ 1407. Br Cl H CH(CH₃)₂ 1408. Br F H CH(CH₃)₂ 1409. Br CH₃ H CH(CH₃)₂ 1410. Br OCH₃ H CH(CH₃)₂ 1411. Br Br H CH(CH₃)₂ 1412. Br CF₃ H CH(CH₃)₂ 1413. Br OCF₃ H CH(CH₃)₂ 1414. Br Cl H n-C₄H₉ 1415. Br F H n-C₄H₉ 1416. Br CH₃ H n-C₄H₉ 1417. Br OCH₃ H n-C₄H₉ 1418. Br Br H n-C₄H₉ 1419. Br CF₃ H n-C₄H₉ 1420. Br OCF₃ H n-C₄H₉ 1421. Br Cl H C(CH₃)₃ 1422. Br F H C(CH₃)₃ 1423. Br CH₃ H C(CH₃)₃ 1424. Br OCH₃ H C(CH₃)₃ 1425. Br Br H C(CH₃)₃ 1426. Br CF₃ H C(CH₃)₃ 1427. Br OCF₃ H C(CH₃)₃ 1428. Br Cl H C₆H₅ 1429. Br F H C₆H₅ 1430. Br CH₃ H C₆H₅ 1431. Br OCH₃ H C₆H₅ 1432. Br Br H C₆H₅ 1433. Br CF₃ H C₆H₅ 1434. Br OCF₃ H C₆H₅ 1435. Br Cl H cyclopropyl 1436. Br F H cyclopropyl 1437. Br CH₃ H cyclopropyl 1438. Br OCH₃ H cyclopropyl 1439. Br Br H cyclopropyl 1440. Br CF₃ H cyclopropyl 1441. Br OCF₃ H cyclopropyl 1442. Br Cl H CH₂-cyclopropyl 1443. Br F H CH₂-cyclopropyl 1444. Br CH₃ H CH₂-cyclopropyl 1445. Br OCH₃ H CH₂-cyclopropyl 1446. Br Br H CH₂-cyclopropyl 1447. Br CF₃ H CH₂-cyclopropyl 1448. Br OCF₃ H CH₂-cyclopropyl 1449. Br Cl H cyclobutyl 1450. Br F H cyclobutyl 1451. Br CH₃ H cyclobutyl 1452. Br OCH₃ H cyclobutyl 1453. Br Br H cyclobutyl 1454. Br CF₃ H cyclobutyl 1455. Br OCF₃ H cyclobutyl 1456. Br Cl H cyclopentyl 1457. Br F H cyclopentyl 1458. Br CH₃ H cyclopentyl 1459. Br OCH₃ H cyclopentyl 1460. Br Br H cyclopentyl 1461. Br CF₃ H cyclopentyl 1462. Br OCF₃ H cyclopentyl 1463. Br Cl H cyclohexyl 1464. Br F H cyclohexyl 1465. Br CH₃ H cyclohexyl 1466. Br OCH₃ H cyclohexyl 1467. Br Br H cyclohexyl 1468. Br CF₃ H cyclohexyl 1469. Br 00F₃ H cyclohexyl 1470. Br H Cl H 1471. Br H F H 1472. Br H CH₃ H 1473. Br H OCH₃ H 1474. Br H Br H 1475. Br H CF₃ H 1476. Br H OCF₃ H 1477. Br H Cl CH₃ 1478. Br H F CH₃ 1479. Br H CH₃ CH₃ 1480. Br H OCH₃ CH₃ 1481. Br H Br CH₃ 1482. Br H CF₃ CH₃ 1483. Br H OCF₃ CH₃ 1484. Br H Cl C₂H₅ 1485. Br H F C₂H₅ 1486. Br H CH₃ C₂H₅ 1487. Br H OCH₃ C₂H₅ 1488. Br. H Br C₂H₅ 1489. Br H CF₃ C₂H₅ 1490. Br H OCF₃ C₂H₅ 1491. Br H Cl n-C₃H₇ 1492. Br H F n-C₃H₇ 1493. Br H CH₃ n-C₃H₇ 1494. Br H OCH3 n-C₃H₇ 1495. Br H Br n-C₃H₇ 1496. Br H CF₃ n-C₃H₇ 1497. Br H OCF₃ n-C₃H₇ 1498. Br H Cl CH(CH₃)₂ 1499. Br H F CH(CH₃)₂ 1500. Br H CH₃ CH(CH₃)₂ 1501. Br H OCH₃ CH(CH₃)₂ 1502. Br H Br CH(CH₃)₂ 1503. Br H CF₃ CH(CH₃)₂ 1504. Br H OCF₃ CH(CH₃)₂ 1505. Br H Cl n-C₄H₉ 1506. Br H F n-C₄H₉ 1507. Br H CH₃ n-C₄H₉ 1508. Br H OCH₃ n-C₄H₉ 1509. Br H Br n-C₄H₉ 1510. Br H CF₃ n-C₄H₉ 1511. Br H OCF₃ n-C₄H₉ 1512. Br H Cl C(CH₃)₃ 1513. Br H F C(CH₃)₃ 1514. Br H CH₃ C(CH₃)₃ 1515. Br H OCH₃ C(CH₃)₃ 1516. Br H Br C(CH₃)₃ 1517. Br H CF₃ C(CH₃)₃ 1518. Br H OCF₃ C(CH₃)₃ 1519. Br H Cl C₆H₅ 1520. Br H F C₆H₅ 1521. Br H CH₃ C₆H₅ 1522. Br H OCH₃ C₆H₅ 1523. Br H Br C₆H₅ 1524. Br H CF₃ C₆H₅ 1525. Br H OCF₃ C₆H₅ 1526. Br H Cl cyclopropyl 1527. Br H F cyclopropyl 1528. Br H CH₃ cyclopropyl 1529. Br H OCH₃ cyclopropyl 1530. Br H Br cyclopropyl 1531. Br H CF₃ cyclopropyl 1532. Br H OCF₃ cyclopropyl 1533. Br H Cl CH₂-cyclopropyl 1534. Br H F CH₂-cyclopropyl 1535. Br H CH₃ CH₂-cyclopropyl 1536. Br H OCH₃ CH₂-cyclopropyl 1537. Br H Br CH₂-cyclopropyl 1538. Br H CF₃ CH₂-cyclopropyl 1539. Br H OCF₃ CH₂-cyclopropyl 1540. Br H Cl cyclobutyl 1541 Br H F cyclobutyl 1542. Br H CH₃ cyclobutyl 1543. Br H OCH₃ cyclobutyl 1544. Br H Br cyclobutyl 1545. Br H CF₃ cyclobutyl 1546. Br H OCF₃ cyclobutyl 1547. Br H Cl cyclopentyl 1548. Br H F cyclopentyl 1549. Br H CH₃ cyclopentyl 1550. Br H OCH₃ cyclopentyl 1551. Br H Br cyclopentyl 1552. Br H CF₃ cyclopentyl 1553. Br H OCF₃ cyclopentyl 1554. Br H Cl cyclohexyl 1555. Br H F cyclohexyl 1556. Br H CH₃ cyclohexyl 1557. Br H OCH₃ cyclohexyl 1558. Br H Br cyclohexyl 1559. Br H CF₃ cyclohexyl 1560. Br H OCF₃ cyclohexyl 1561. CH₃ Cl H H 1562. CH₃ F H H 1563. CH₃ CH₃ H H 1564. CH₃ OCH₃ H H 1565. CH₃ Br H H 1566. CH₃ CF₃ H H 1567. CH₃ OCF₃ H H 1568. CH₃ Cl H CH₃ 1569. CH₃ F H CH₃ 1570. CH₃ CH₃ H CH₃ 1571. CH₃ Br H CH₃ 1572. CH₃ CF₃ H CH₃ 1573. CH₃ OCF₃ H CH₃ 1574. CH₃ Cl H C₂H₅ 1575. CH₃ F H C₂H₅ 1576. CH₃ CH₃ H C₂H₅ 1577. CH₃ Br H C₂H₅ 1578. CH₃ CF₃ H C₂H₅ 1579. CH₃ OCF₃ H C₂H₅ 1580. CH₃ Cl H n-C₃H₇ 1581. CH₃ F H n-C₃H₇ 1582. CH₃ CH₃ H n-C₃H₇ 1583. CH₃ Br H n-C₃H₇ 1584. CH₃ CF₃ H n-C₃H₇ 1585. CH₃ OCF₃ H n-C₃H₇ 1586. CH₃ Cl H CH(CH₃)₂ 1587. CH₃ F H CH(CH₃)₂ 1588. CH₃ CH₃ H CH(CH₃)₂ 1589. CH₃ Br H CH(CH₃)₂ 1590. CH₃ CF₃ H CH(CH₃)₂ 1591. CH₃ OCF₃ H CH(CH₃)₂ 1592. CH₃ Cl H n-C₄H₉ 1593. CH₃ F H n-C₄H₉ 1594. CH₃ CH₃ H n-C₄H₉ 1595. CH₃ Br H n-C₄H₉ 1596. CH₃ CF₃ H n-C₄H₉ 1597. CH₃ OCF₃ H n-C₄H₉ 1598. CH₃ Cl H C(CH₃)₃ 1599. CH₃ F H C(CH₃)₃ 1600. CH₃ CH₃ H C(CH₃)₃ 1601. CH₃ Br H C(CH₃)₃ 1602. CH₃ CF₃ H C(CH₃)₃ 1603. CH₃ OCF₃ H C(CH₃)₃ 1604. CH₃ Cl H C₆H₅ 1605. CH₃ F H C₆H₅ 1606. CH₃ CH₃ H C₆H₅ 1607. CH₃ Br H C₆H₅ 1608. CH₃ CF₃ H C₆H₅ 1609. CH₃ OCF₃ H C₆H₅ 1610. CH₃ Cl H cyclopropyl 1611. CH₃ F H cyclopropyl 1612. CH₃ CH₃ H cyclopropyl 1613. CH₃ Br H cyclopropyl 1614. CH₃ CF₃ H cyclopropyl 1615. CH₃ OCF₃ H cyclopropyl 1616. CH₃ Cl H CH₂-cyclopropyl 1617. CH₃ F H CH₂-cyclopropyl 1618. CH₃ CH₃ H CH₂-cyclopropyl 1619. CH₃ Br H CH₂-cyclopropyl 1620. CH₃ CF₃ H CH₂-cyclopropyl 1621. CH₃ OCF₃ H CH₂-cyclopropyl 1622. CH₃ Cl H cyclobutyl 1623. CH₃ F H cyclobutyl 1624. CH₃ CH₃ H cyclobutyl 1625. CH₃ Br H cyclobutyl 1626. CH₃ CF₃ H cyclobutyl 1627. CH₃ OCF₃ H cyclobutyl 1628. CH₃ Cl H cyclopentyl 1629. CH₃ F H cyclopentyl 1630. CH₃ CH₃ H cyclopentyl 1631. CH₃ Br H cyclopentyl 1632. CH₃ CF₃ H cyclopentyl 1633. CH₃ OCF₃ H cyclopentyl 1634. CH₃ Cl H cyclohexyl 1635. CH₃ F H cyclohexyl 1636. CH₃ CH₃ H cyclohexyl 1637. CH₃ Br H cyclohexyl 1638. CH₃ CF₃ H cyclohexyl 1639. CH₃ OCF₃ H cyclohexyl 1640. CH₃ H Cl H 1641. CH₃ H F H 1642. CH₃ H CH₃ H 1643. CH₃ H Br H 1644. CH₃ H CF₃ H 1645. CH₃ H OCF₃ H 1646. CH₃ H Cl CH₃ 1647. CH₃ H F CH₃ 1648. CH₃ H CH₃ CH₃ 1649. CH₃ H Br CH₃ 1650. CH₃ H CF₃ CH₃ 1651. CH₃ H OCF₃ CH₃ 1652. CH₃ H Cl C₂H₅ 1653. CH₃ H F C₂H₅ 1654. CH₃ H CH₃ C₂H₅ 1655. CH₃ H Br C₂H₅ 1656. CH₃ H CF₃ C₂H₅ 1657. CH₃ H OCF₃ C₂H₅ 1658. CH₃ H Cl n-C₃H₇ 1659. CH₃ H F n-C₃H₇ 1660. CH₃ H CH₃ n-C₃H₇ 1661. CH₃ H Br n-C₃H₇ 1662. CH₃ H CF₃ n-C₃H₇ 1663. CH₃ H OCF₃ n-C₃H₇ 1664. CH₃ H Cl CH(CH₃)₂ 1665. CH₃ H F CH(CH₃)₂ 1666. CH₃ H CH₃ CH(CH₃)₂ 1667. CH₃ H Br CH(CH₃)₂ 1668. CH₃ H CF₃ CH(CH₃)₂ 1669. CH₃ H OCF₃ CH(CH₃)₂ 1670. CH₃ H Cl n-C₄H₉ 1671. CH₃ H F n-C₄H₉ 1672. CH₃ H CH₃ n-C₄H₉ 1673. CH₃ H Br n-C₄H₉ 1674. CH₃ H CF₃ n-C₄H₉ 1675. CH₃ H OCF₃ n-C₄H₉ 1676. CH₃ H Cl C(CH₃)₃ 1677. CH₃ H F C(CH₃)₃ 1678. CH₃ H CH₃ C(CH₃)₃ 1679. CH₃ H Br C(CH₃)₃ 1680. CH₃ H CF₃ C(CH₃)₃ 1681. CH₃ H OCF₃ C(CH₃)₃ 1682. CH₃ H Cl C₆H₅ 1683. CH₃ H F C₆H₅ 1684. CH₃ H CH₃ C₆H₅ 1685. CH₃ H Br C₆H₅ 1686. CH₃ H CF₃ C₆H₅ 1687. CH₃ H OCF₃ C₆H₅ 1688. CH₃ H Cl cyclopropyl 1689. CH₃ H F cyclopropyl 1690. CH₃ H CH₃ cyclopropyl 1691. CH₃ H Br cyclopropyl 1692. CH₃ H CF₃ cyclopropyl 1693. CH₃ H OCF₃ cyclopropyl 1694. CH₃ H Cl CH₂-cyclopropyl 1695. CH₃ H F CH₂-cyclopropyl 1696. CH₃ H CH₃ CH₂-cyclopropyl 1697. CH₃ H Br CH₂-cyclopropyl 1698. CH₃ H CF₃ CH₂-cyclopropyl 1699. CH₃ H OCF₃ CH₂-cyclopropyl 1700. CH₃ H Cl cyclobutyl 1701. CH₃ H F cyclobutyl 1702. CH₃ H CH₃ cyclobutyl 1703. CH₃ H Br cyclobutyl 1704. CH₃ H CF₃ cyclobutyl 1705. CH₃ H OCF₃ cyclobutyl 1706. CH₃ H Cl cyclopentyl 1707. CH₃ H F cyclopentyl 1708. CH₃ H CH₃ cyclopentyl 1709. CH₃ H Br cyclopentyl 1710. CH₃ H CF₃ cyclopentyl 1711. CH₃ H OCF₃ cyclopentyl 1712. CH₃ H Cl cyclohexyl 1713. CH₃ H F cyclohexyl 1714. CH₃ H CH₃ cyclohexyl 1715. CH₃ H Br cyclohexyl 1716. CH₃ H CF₃ cyclohexyl 1717. CH₃ H OCF₃ cyclohexyl

Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ib (≡I where R^(a)═R^(e)═H, X═O, Y═O, R¹═H, R³═H and n=0) where R^(b), R^(c), R^(d) and R² have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ib.1 to Ib.1717 in which the variables R^(b), R^(c), R^(d) and R² together have the meanings given in one row of Table 1.

Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ic (≡I where R^(a)═R^(e)═H, X═O, Y═O, R¹═H, R³═C₂H₅ and n=0) where R^(b), R^(c), R^(d) and R² have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ic.1 to Ic.1717 in which the variables R^(b), R^(c), R^(d) and R² together have the meanings given in one row of Table 1.

Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Id (≡I where X═O, Y═O, R¹═H, R³═CH(CH₃)₂ and n=0) where R^(b), R^(c), R^(d) and R² have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Id.1 to Id.1717 in which the variables R^(b), R^(c), R^(d) and R² together have the meanings given in one row of Table 1.

Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ie (≡I where X═O, Y═O, R¹═H, R³═H, A═O and n=1) where R^(b), R^(c), R^(d) and R² have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ie.1 to Ie.1717 in which the variables R^(b), R^(c), R^(d) and R² together have the meanings given in one row of Table 1.

Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula If (≡I where X═O, Y═O, R¹═H, R³═CH₃, A═O and n=1) where R^(b), R^(c), R^(d) and R² have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds If.1 to If.1717 in which the variables R^(b), R^(c), R^(d) and R² together have the meanings given in one row of Table 1.

Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ig (≡I where X═O, Y═O, R¹═H, R³ ═C₂H₅, A═O and n=1) where R^(b), R^(c), R^(d) and R² have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ig.1 to Ig.1717 in which the variables R^(b), R^(c), R^(d) and R² together have the meanings given in one row of Table 1.

Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ih (≡I where X═O, Y═O, R¹H, R³═CH(CH₃)₂, A═O and n=1) where R^(b), R^(c), R^(d) and R² have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ih.1 to Ih.1717 in which the variables R^(b), R^(c), R^(d) and R² together have the meanings given in one row of Table 1.

Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ii (≡I where X═O, Y═O, R¹═H, R³═H, n=1 and A═NR¹² where R¹²═H) where R^(b), R^(c), R^(d) and R² have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ii.1 to Ii.1717 in which the variables R^(b), R^(c), R^(d) and R² together have the meanings given in one row of Table 1.

Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ij (≡I where X═O, Y═O, R¹═H, R³═CH₃, n=1 and A═NR¹² where R¹²═H) where R^(b), R^(c), R^(d) and R² have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ij.1 to Ij.1717 in which the variables R^(b), R^(c), R^(d) and R² together have the meanings given in one row of Table 1.

Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ik (≡I where X═O, Y═O, R¹═H, R³═C₂H₅, n=1 and A═NR¹² where R¹²═H) where R^(b), R^(c), R^(d) and R² have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ik.1 to Ik.1717 in which the variables R^(b), R^(c), R^(d) and R² together have the meanings given in one row of Table 1.

Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula II (≡I where X═O, Y═O, R¹═H, R³═CH(CH₃)₂, n=1 and A═NR¹² where R¹²═H) where R^(b), R^(c), R^(d) and R² have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Il.1 to Il.1717 in which the variables R^(b), R^(c), R^(d) and R² together have the meanings given in one row of Table 1.

Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Im (≡I where X═O, Y═O, R¹═H, R³═H, n=1 and A═NR¹² where R¹²═CH₃) where R^(b), R^(c), R^(d) and R² have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Im.1 to Im.1717 in which the variables R^(b), R^(c), R^(d) and R² together have the meanings given in one row of Table 1.

Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula In (≡I where X═O, Y═O, R¹═H, R³═CH₃, n=1 and A═NR¹² where R¹²═CH₃) where R^(b), R^(c), R^(d) and R² have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds In.1 to In.1717 in which the variables R^(b), R^(c), R^(d) and R² together have the meanings given in one row of Table 1.

Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Io (≡I where X═O, Y═O, R¹═H, R³═C₂H₅, n=1 and A═NR¹² where R¹²═CH₃) where R^(b), R^(c), R^(d) and R² have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Io.1 to Io.1717 in which the variables R^(b), R^(c), R^(d) and R² together have the meanings given in one row of Table 1.

Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ip (≡I where X═O, Y═O, R¹═H, R³═CH(CH₃)₂, n=1 and A═NR¹² where R¹²═CH₃) where R^(b), R^(c), R^(d) and R² have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ip.1 to Ip.1717 in which the variables R^(b), R^(c), R^(d) and R² together have the meanings given in one row of Table 1.

The 1-phenylpyrrolidin-2-one-3-carboxamides of the formula I according to the invention can be prepared, for example, by one of the processes A to G described below.

A) Amidation of a Carboxylic Acid II or a Carboxylic Acid Derivative of II

The preparation of the compound I according to the invention can be carried out, for example, according to Scheme 1 by reacting an activated form of a pyrrolidine-3-carboxylic acid of the formula II with an amine III.

In Scheme 1, the variables R¹, X, R^(a), R^(b), R^(c), R^(d), R^(e), A, n, R² and R³ are as defined above. Such reactions are known, for example from WO 01/83459, and can be applied in an analogous manner to the reaction illustrated in Scheme 1. The carboxylic acid II is preferably initially activated by carrying out the reaction in the presence of a coupling agent. Suitable coupling agents are, for example, N,N′-carbonyldiimidazole or carbodiimides, such as dicyclohexylcarbodiimide. These compounds are generally employed in an at least equimolar amount and up to a four-fold excess, based on the carboxylic acid II. If appropriate, it may be advantageous to carry out the reaction of the carboxylic acid II with the coupling agent in the presence of a catalytic amount of a tertiary aminopyridine, such as 4-dimethylaminopyridine (DMAP). In this case, the amount of aminopyridine added is preferably 5 to 10 mol %, based on the carboxylic acid II. The reaction is usually carried out in a solvent. Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, ethers, for example dialkyl ethers, such as diethyl ether, methyl tert-butyl ether, or cyclic ethers, such as tetrahydrofuran or dioxane, carboxamides, such as dimethylformamide, N-methyllactams, such as N-methylpyrrolidone, nitriles, such as acetonitrile, aromatic hydrocarbons, such as toluene, or mixtures of these.

The molar ratio of amine III to carboxylic acid II is generally at least 0.9:1, preferably at least 1:1. If appropriate, it may be advantageous to employ the amine in a slight excess, for example in an excess of up to 30%, based on the carboxylic acid II.

In general, the reaction temperature is in the range from 0° C. to the boiling point of the solvent.

Alternatively, the carboxylic acid II can initially be activated by converting it into its acid halide, preferably its acid chloride. Means for this purpose are known, for example from U.S. Pat. No. 4,874,422. Suitable compounds are inorganic acid halides, preferably acid chlorides, such as thionyl chloride, phosphoryl chloride phosphorus pentachloride or phosphorus trichloride, and organic acid chlorides, such as oxalyl chloride. The acid halide of II formed can be isolated and then be reacted with the amine III. It is also possible to react the acid chloride of II formed directly, without isolation, with the amine III. If appropriate, the reactivity of the acid halide is enhanced by adding catalytic amounts of an N,N-dialkylcarboxamide, such as dimethylformamide. The halogenating agent is usually employed in an at least equimolar amount, based on the carboxylic acid II. The acid halides thionyl chloride, phosphorus trichloride or phosphoryl chloride can simultaneously act as solvent. Suitable solvents are furthermore-solvents which are inert under the reaction conditions, for example chlorinated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, aromatic hydrocarbons, such as benzene or toluene, aliphatic and cycloaliphatic hydrocarbons, such as hexane, petroleum ether, cyclohexane, and mixtures thereof. The reaction temperature is generally between room temperature and the boiling point of the solvent. After the reaction has ended, excess halogenating agent is generally removed. The resulting acid halide of II is then reacted with the amine III. In general, the amine III is dissolved in the solvent which was also used for preparing the carbonyl halide, unless the solvent is one of the acid halides mentioned above.

If appropriate, the reaction is carried out in the presence of an auxiliary base which is preferably employed in an equimolar amount or an up to four-fold excess, based on the carboxylic acid II. Suitable bases are, for example, amines such as 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), pyridine, α-, β-, γ-lutidine or triethylamine.

It is, of course, also possible to use other methods for activating the carboxylic acid II. Such methods are described in the prior art, for example in J. Falbe, Houben Weyl, Methoden der Organischen Chemie [Methods of organic chemistry], Vol. E5, 4th Ed., 1985, p. 941 ff.

In a further process variant, the corresponding carboxylic acid ester of II (carboxylic acid ester VI), in particular the C₁-C₄-alkyl ester of II and especially the methyl or ethyl ester of II, is reacted with the amine III, if appropriate in the presence of a base. Regarding a suitable base, solvent and reaction temperatures, reference is made to what was said above. The preparation of the carboxylic acid ester VI is described below.

Compounds of the formula II where R¹═H can be prepared, for example, similarly to a process described in Journal of Heterocyclic Chemistry, 3 (1966), 311. The synthesis is shown in Scheme 2.

In Scheme 2, the variables R^(a), R^(b), R^(c), R^(d), R^(e) are as defined above and R is C₁-C₄-alkyl. The reaction of the aniline compound IV with butyrolactone is usually carried out in the presence of an inorganic acid, such as sulfuric acid, phosphoric acid or hydrochloric acid, or in the presence of an organic acid, such as acetic acid. The reaction can be carried out in the absence of a solvent or in the presence of a solvent. Suitable solvents are all solvents which are inert under the reaction conditions. However, the reaction is preferably carried out in the absence of a solvent. If the reaction is carried out in the absence of a solvent, the butyrolactone is employed in an excess, based on the aniline IV. The reaction temperatures are generally in the range of from 20° C. to the boiling point of the solvent.

In the next step, the resulting pyrrolidinone V is generally reacted without further purification, for example with a carbonate (RO)₂CO or a synthetic equivalent, such as a chloroformic ester. To this end, the pyrrolidinone V is generally initially converted into the corresponding enolate by treatment with a suitable base. Suitable bases include in particular organolithium compounds, such as n-butyllithium, tert-butyllithium and phenyllithium, lithium amides, such as lithium diisopropylamide, and alkali metal hydrides, such as sodium hydride. The reaction is generally carried out in an organic solvent. Suitable solvents are inert solvents, such as aliphatic and cycloaliphatic hydrocarbons, such as hexane, petroleum ether, cyclohexane, ethers, for example dialkyl ethers, such as diethyl ether, methyl tert-butyl ether, or cyclic ethers, such as tetrahydrofuran or dioxane, and also mixtures of these. In general, the deprotonation of the compound V is carried out at low temperatures to about room temperature, preferably at about 0° C. To this end, the base is employed in an at least equimolar amount, preferably a 1.1- to 4-fold molar excess, based on the compound V.

The subsequent introduction of the alkoxycarbonyl group is carried out, for example, using a carbonic acid diester, such as dimethyl carbonate or diethyl carbonate. The carbonic acid diester and the enolate of the compound V are usually employed in equimolar amounts. It is, of course, possible for one of the two reactants to be employed in a slight excess. The temperature required for the reaction is generally in the range of from 0° C. to the boiling point of the solvent.

The carboxylic acid ester VI is then hydrolyzed by known methods (see, for example, Organikum, 17th Edition, VEB Deutscher Verlag der Wissenschaften, 1988, p. 415) to give the carboxylic acid II. The hydrolysis can be carried out either in acidic medium using strong mineral acids, such as concentrated hydrochloric acid or sulfuric acid, or organic acids, such as glacial acetic acid, or mixtures of these in the presence of water, or in alkaline medium using bases, such as alkali metal hydroxide, for example sodium hydroxide or potassium hydroxide, if appropriate in the presence of water.

Suitable solvents both for acidic and basic hydrolysis of esters are, for example, ethers, for example dialkyl ethers, such as diethyl ether, methyl tert-butyl ether, or cyclic ethers, such as tetrahydrofuran or dioxane, alcohols, water and mixtures of these solvents. The reaction temperature is usually between room temperature and the boiling point of the solvent.

The compounds II can furthermore be prepared by aminoethylation of malonic acid esters VII in which R¹ is as defined above and R is C₁-C₄-alkyl with phenylaziridines VII and subsequent hydrolysis. The synthesis is shown in Scheme 3 and can be carried out similarly to known methods as described, for example, in Archiv der Pharmazie (Weinheim) 302(4) (1969), 253, Justus Liebigs Ann. Chem. 716 (1968), 121-126 or in Angew. Chem. 74, (1962), 694.

The reaction is generally carried out in the presence of LiH/LiI in a solvent. Suitable solvents include aromatic solvents, such as benzene, toluene or xylene. Frequently, the aziridine VII and the malonic acid ester are employed in approximately equimolar amounts. It may be advantageous to employ an excess of malonic acid ester VIII, preferably an excess of up to 30%, based on the aziridine VII. The resulting ester VIa is then converted according to known methods by hydrolysis in acidic or alkaline medium into the corresponding carboxylic acids II. With regard to ester hydrolysis, reference is made to what was said above.

Compounds of the formula II in which R¹ is H can furthermore be prepared similarly to a process described in JP 2000143624-A. To this end, anilines IV are reacted with 1,1-cyclopropanedicarboxylic acid. The synthesis route is shown in Scheme 4. The reaction is usually carried out in water or in an aliphatic nitrile, such as acetonitrile, or in mixtures thereof with water, at temperatures between 40 and 100° C.

Compounds of the formula II in which R¹ is H can furthermore be obtained similarly to processes described in J. Am. Chem. Soc. 97 (1975), 3239 or Organic Synthesis 60, (1981), 66. The reaction of the aniline IV with the dioxaspirooctanedione IX gives the carboxylic acid II. The synthesis route is shown in Scheme 5.

B) Linking a Pyrrolidinone X to an Aromatic Compound XI

Compounds of the formula I can furthermore be prepared by reacting suitably substituted pyrrolidinones X with aromatic compounds of the formula XI according to the synthesis shown in Scheme 6.

In Scheme 6, the variables R^(a), R^(b), R^(c), R^(d), R^(d), R^(e), X, Y, A, n, R¹, R² and R³ are as defined above. Z is halogen, preferably fluorine, chlorine or bromine, or B(OH)₂, B(OR′)₂ or Sn(R′)₃. In these radicals, R′ is aryl, such as phenyl, or C₁-C₁₀-alkyl.

The reaction is preferably carried out in a solvent, in particular a polar aprotic solvent, such as dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, dimethylacetamide, an ether, such as diethyl ether, tetrahydrofuran or dioxane, and mixtures of these solvents.

In general, the reaction is carried out at temperatures above room temperature, preferably in the range from 50 to 200° C. To this end, the compounds of the formulae X and XI are preferably employed in approximately equimolar amounts. It is, of course, also possible to use an excess of one of the components, the excess preferably being not more than 50 mol %, in particular not more than 20 mol %, based on the component which is present in a substoichiometric amount.

The compounds I according to the invention are furthermore obtained by coupling XI (for example Z=Cl, Br, I, B(OR)₂, SnR₃) with a pyrrolidinone X, preferably in the presence of catalytically active amounts of a palladium, copper or nickel compound, if appropriate in the presence of a base, in an organic solvent or a mixture of a solvent with water, at room temperature or elevated temperatures. Processes for coupling a phenylboronic acid are described, for example, in WO 02/42275.

Suitable palladium catalysts are, in addition to palladium carboxylates, such as palladium(II) acetate, also palladium/phosphine complexes, such as tetrakistriphenylphosphinepalladium, bistriphenylphosphinepalladium(II) chloride, bis(1,2-diphenylphosphinoethane)palladium(II) chloride, bis(1,3-diphenylphosphinopropane)palladium(II) chloride, bis(1,4-diphenylphosphinobutane)palladium(II) chloride and bis(diphenylphosphino)ferrocenylpalladium(II) chloride. However, it is also possible to react palladium halides such as palladium(II) chloride in situ with phosphine ligands, giving the catalytically active complexes. Suitable phosphine ligands are, for example, arylphosphines which are unsubstituted or substituted in the ortho-, meta- or para-position by halogen, alkyl and/or SO₃H, such as triphenylphosphine, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, bis(diphenylphosphino)ferrocene, hetarylphosphines, such as trifurylphosphine or tripyridylphosphine.

Suitable Ni catalysts are nickel(II) acetylacetonate alone or in combination with the abovementioned phosphine ligands, or Ni(II) acetylacetonate with imidazolium carbene ligands, and also complexes of nickel(II) salts with the above mentioned phosphine ligands, for example bis(triphenylphosphine)nickel(II) chloride, [1,3-bis(diphenylphosphino)propane]nickel(II) chloride, [1,4-bis(diphenylphosphino)butane]nickel(II) chloride and [bis(diphenylphosphino)ferrocene]nickel(II) chloride.

Suitable copper compounds are, in particular, copper(I) compounds, such as CuCl, CuBr and the like.

The catalyst is usually employed in substoichiometric amounts, preferably of 0.001-0.8 equivalents and particularly preferably of 0.01 to 0.5 equivalents, based on the pyrrolidinone XI used.

If appropriate, it may be advantageous to convert the compound X initially with a base into its salt. Suitable bases are, for example, alkali metal hydrides, such as sodium hydride, and sodium alkoxides, such as sodium methoxide and sodium ethoxide, lithium amides, such as lithium diisopropylamide, and also organolithium compounds, such as butyllithium and phenyllithium.

The molar ratio of compound XI to compound X is preferably in the range from 0.95:1 to 1:1.5.

Suitable bases are, if required, alkali metal and alkaline earth metal hydroxides, alkali metal (bi)carbonates and alkali metal phosphates, such as NaOH, NaHCO₃, Na₂CO₃, KHCO₃, K₂CO₃, Ba(OH)₂, K₃PO₄, alkali metal, alkaline earth metal, thallium and transition metal alkoxides, such as sodium ethoxide and thallium ethoxide. Other suitable bases are alkali metal fluorides, such as potassium fluoride, cesium fluoride, ammonium fluorides and tetrabutylammonium fluoride. The base is usually employed in an approximately stoichiometric amount or in up to 10-fold excess, based on the compound II.

Suitable solvents are organic solvents, such as DMF, dimethylacetamide, toluene, tetrahydrofuran (THF), dioxane and dimethoxyethane. If the coupling is carried out with boronic acid, the abovementioned solvents can also be employed in a mixture with water, for example in a ratio of about 5:1 to 1:5, preferably in a ratio of about 2:1 to 1:2 and in particular of about 1:1.

The reaction temperature is usually above the melting point and can be up to the boiling point of the solvent. It is preferably in the range between 50 and 150° C.

The pyrrolidino compounds X can be prepared by customary processes, for example analogously to the procedure described in process A.

C) Alkylation of Compounds of the Formula I in which R¹═H

Compounds of the formula I in which R¹ is hydrogen can be prepared according to general methods by treatment with an alkylation agent R¹-L in compounds of the formula I in which R¹ is not hydrogen. The synthesis route is shown in Scheme 7.

In Scheme 7, the variables R¹, R^(a), R^(b), R^(c), R^(d), R^(d), R^(e), X, Y, A, n, R¹, R² and R³ are as defined above. L is a nucleophilically displaceable leaving group, such as halogen, for example chlorine, bromine, iodine, or imidazolyl, carboxylate, such as acetate, arylsulfonate or alkylsulfonate, for example mesylate or triflate. The reaction is usually carried out in the presence of a base. Suitable bases include alkali metal or alkaline earth metal hydroxides, metal hydrides, such as alkali metal hydrides, for example sodium hydride, tertiary alkylamines, such as triethylamine, aromatic amines, such as pyridine, α-, β-, γ-lutidine, lithium diisopropylamide.

Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide.

In general, the reaction temperature is in the range from 0° C. to the boiling point of the reaction mixture.

D) Sulfurization of the Compounds of the Formula I in which X or Y is Oxygen.

Compounds of the formula I in which X or Y is oxygen can be prepared according to general methods by treatment with a sulfurizing agent in compounds of the formula I in which X or Y is sulfur. This synthesis route is illustrated in Scheme 8.

In Scheme 8, the variables R^(a), R^(b), R^(c), R^(d), R^(d), R^(e), X, Y, A, n, R¹, R² and R³ are as defined above. Examples of suitable sulfurizing agents are phosphorus(V) sulfides, organotin sulfides, and also organophosphorus sulfides (see also J. March, Advanced Organic Synthesis, 2nd Edition, Wiley Interscience 1985, p. 794 and the literature cited therein). Particularly suitable sulfurizing agents are phosphorus(V) sulfide and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithia-diphosphetane-2,4-dithione (“Lawesson's reagent”). Sulfurization processes are described, for example, in WO 95/33718. The reaction can be carried out in a solvent or neat. Suitable solvents are all solvents which are inert under the reaction conditions, for example aromatic hydrocarbons, such as benzene, toluene, xylene, chlorobenzene, basic solvents, such as pyridine, ethers, such as diethyl ether, 1,2-dimethoxyethane or tetrahydrofuran, etc. The temperatures required for the reaction are generally above room temperature and in particular in the range of from 50° C. to the boiling point of the reaction mixture.

E) Condensation of an Anilide XII

A further route to the compounds I according to the invention is the reaction of an anilide XII with a suitable difunctional compound L-CH₂—CH₂-L′ with ring closure according to Scheme 9.

In Scheme 9, the variables R^(a), R^(b), R^(c), R^(d), R^(d), R^(e), X, Y, A, n, R¹, R² and R³ are as defined above, L is as defined in C) and L′ has the meaning of L.

The cyclization is carried out in the presence of a base. Suitable bases are all bases mentioned under C). In general, the reaction is carried out in an inert solvent. Suitable solvents are in particular chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide. The starting material XII and the difunctional compound L-CH₂—CH₂-L′ are expediently employed in approximately equimolar amounts; however, to optimize the conversion, it may be advantageous to use an excess of one of the two components. The reaction is generally carried out at a temperature between room temperature and the boiling point of the reaction mixture.

The starting materials XII can be prepared in two steps similarly to the process described in Synlett 12 (1969), 1209. In the first step, an isocyanate XIII is reacted with meldrum acid (2,2-dimethyl-1,3-dioxane-4,6-dione). In the second step, the resulting product is then reacted with a suitable amine III. In Scheme 10, the variables R^(a), R^(b), R^(c), R^(d), R^(d), R^(e), X, Y, A, n, R¹, R² and R³ are as defined above.

F) Condensations F.1 Condensation of Anilines IV with tetrahydro-2-furanones XIV

The compounds I according to the invention can be prepared, for example, by condensing anilines IV with tetrahydro-2-furanones XIV according to the synthesis route shown in Scheme 11. Analogous reactions are known, for example from Tetrahedron Letters, 31 (21) (1990), 2991, and can be applied to the preparation of the compounds according to the invention.

In Scheme 11, the variables R^(a), R^(b), R^(c), R^(d), R^(d), R^(e), X, Y, A, n, R¹, R² and R³ are as defined above. The reaction of the anilines IV is usually carried out in a carboxylic acid, such as acetic acid, at temperatures in the range from 0° C. to 100° C. In general, the starting materials are employed in equimolar amounts, or one of the two components is employed in excess.

F.2 Condensation of Anilines IV with Carboxylic Acid Derivatives XV and Subsequent Cyclization

The compounds I according to the invention can be prepared, for example, by condensing anilines IV with carboxylic acid derivatives XV according to the synthesis route shown in Scheme 12.

In Scheme 12, the variables R^(a), R^(b), R^(c), R^(d), R^(d), R^(e), X, Y, A, n, R¹, R² and R³ are as defined above. L is as defined in C) and L′ has the meaning of L. The reaction of the aniline IV with the carboxylic acid derivative XV is usually carried out in the presence of a base. Suitable bases are, for example, amines, such as 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), pyridine or triethylamine. The base is usually employed in up to six-fold excess, based on the carboxylic acid derivative XV. The reaction is generally carried out in a solvent. Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, ethers, for example dialkyl ethers, such as diethyl ether, methyl tert-butyl ether, or cyclic ethers, such as tetrahydrofuran or dioxane, carbonamides, such as dimethylformamide, N-methyllactams, such as N-methylpyrrolidone, nitrites, such as acetonitrile, aromatic hydrocarbons, such as toluene, aromatic amines, such as pyridine, or mixtures of these. In general, the reaction temperature is in a range of from 0° C. to the boiling point of the solvent.

G) Reaction of a Pyrrolidinone XVI with an iso(thio)cyanate XVII

Compounds of the formula I can be prepared by reacting pyrrolidinones XVI with an iso(thio)cyanate XVII in the presence of a base according to the synthesis route shown in Scheme 13. Such reactions are known, for example, from U.S. Pat. No. 5,185,349.

In Scheme 13, the variables R^(a), R^(b), R^(c), R^(d), R^(d), R^(e), X, Y and R¹ are as defined above. R³′ has the meanings mentioned for R³ which are different from hydrogen. To prepare compounds I where R³═H, preference is given to using the salt of an isocyanate or isothiocyanate, for example sodium iso(thio)cyanate or potassium iso(thio)cyanate.

Suitable bases include alkali metal hydrides, such as sodium hydride or potassium hydride, organolithium compounds, such as lithium diisopropylamide. In general, the reaction is carried out in a solvent. Suitable solvents include ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, 1,4-dioxane, anisole, glycol ethers, such as dimethyl glycol ether, hydrocarbons, such as hexane, petroleum ether or mixtures of these.

The compounds I and their agriculturally useful salts are suitable—both as isomer mixtures and in the form of the pure isomers—as herbicides. The herbicidal compositions comprising I permit very good control of plant growth on uncultivated areas. In crops such as wheat, rice, corn, soybean and cotton, they are effective against broad-leaved weeds and harmful grasses without significantly damaging the crops. This effect occurs in particular at low application rates.

Depending on the particular application method, the compounds I or the herbicidal compositions comprising them may be used in a further number of crops for eliminating unwanted plants. Suitable are, for example, the following crops:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

The compounds I may also be used in crops which are tolerant to the action of herbicides as a result of breeding, including the use of genetic engineering methods.

The compounds I or the herbicidal compositions comprising them can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, including highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusting agents, broadcasting agents or granules, by spraying, nebulizing, dusting, broadcasting or pouring, or for seed dressing or mixing with the seed. The application forms depend on the intended uses; they should in any case ensure very fine distribution of the active ingredients according to the invention.

The herbicidal compositions comprise a herbicidally effective amount of at least one active compound of the formula I and auxiliaries which are usually used in formulating crop protection agents.

Suitable inert auxiliaries are essentially:

mineral oil fractions having a medium to high boiling point, such as kerosine and diesel oil, and coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffins, tetrahydronaphthalene, alkylated naphthalenes and derivatives thereof, alkylated benzenes and derivatives thereof, alcohols, such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones, such as cyclohexanone, and strongly polar solvents, for example amines, such as N-methylpyrrolidone, and water.

Aqueous application forms can be prepared from emulsion concentrates, from suspensions, pastes, wettable powders or water-dispersible granules by adding water. For the preparation of emulsions, pastes or oil dispersions, the 1-phenylpyrrolidin-2-onecarboxamides I, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, adherents, dispersants or emulsifiers. However, it is also possible to prepare concentrates which consist of active ingredient, wetting agent, adherent, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.

Suitable surfactants are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, e.g. lignin-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkylsulfonates and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ether; condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors and methylcellulose.

Powders, broadcasting agents and dusting agents can be prepared by mixing or milling the active ingredients together with a solid carrier.

Granules, for example coated, impregnated and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, milled plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and vegetable products, such as grain flour, bark meal, wood meal and nutshell meal, cellulosic powders and other solid carriers.

The concentrations of the active ingredients I in the ready-to-use formulations may be varied within wide ranges. In general, the formulations comprise from about 0.001 to 98, preferably from 0.01 to 95, % by weight of at least one active ingredient I. The active ingredients are used in a purity of from 90 to 100%, preferably from 95 to 100% (according to the NMR spectrum).

The compounds I according to the invention can be formulated, for example, as follows:

-   I. 20 parts by weight of a compound I are dissolved in a mixture     which consists of 80 parts by weight of alkylated benzene, 10 parts     by weight of the adduct of from 8 to 10 mol of ethylene oxide with 1     mol of N-monoethanololeamide, 5 parts by weight of the calcium salt     of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct     of 40 mol of ethylene oxide with 1 mol of castor oil. By pouring the     solution into 100,000 parts by weight of water and finely     distributing it therein, an aqueous dispersion which comprises 0.02%     by weight of the active ingredient is obtained. -   II. 20 parts by weight of a compound I are dissolved in a mixture     which consists of 40 parts by weight of cyclohexanone, 30 parts by     weight of isobutanol, 20 parts by weight of the adduct of 7 mol of     ethylene oxide with 1 mol of isooctylphenol and 10 parts by weight     of the adduct of 40 mol of ethylene oxide with 1 mol of castor oil.     By pouring the solution into 100,000 parts by weight of water and     finely distributing it therein, an aqueous dispersion which     comprises 0.02% by weight of the active ingredient is obtained. -   III. 20 parts by weight of a compound I are dissolved in a mixture     which consists of 25 parts by weight of cyclohexanone, 65 parts by     weight of a mineral oil fraction boiling within the range from 210     to 280° C. and 10 parts by weight of the adduct of 40 mol of     ethylene oxide with 1 mol of castor oil. By pouring the solution     into 100,000 parts by weight of water and finely distributing it     therein, an aqueous dispersion which comprises 0.02% by weight of     the active ingredient is obtained. -   IV. 20 parts by weight of a compound I are thoroughly mixed with 3     parts by weight of the sodium salt of     diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the     sodium salt of a lignosulfonic acid obtained from a sulfite waste     liquor and 60 parts by weight of silica gel powder, and the mixture     is milled in a hammer mill. By finely distributing the mixture in     20,000 parts by weight of water, a spray liquor which comprises 0.1%     by weight of the active ingredient is obtained. -   V. 3 parts by weight of a compound I are mixed with 97 parts by     weight of finely divided kaolin. A dusting agent which comprises 3%     by weight of the active ingredient is obtained in this manner. -   VI. 20 parts by weight of a compound I are thoroughly mixed with 2     parts by weight of the calcium salt of dodecylbenzenesulfonic acid,     8 parts by weight of fatty alcohol polyglycol ether, 2 parts by     weight of sodium salt of a phenol/urea/formaldehyde condensate and     68 parts by weight of a paraffinic mineral oil. A stable oily     dispersion is obtained. -   VII. 1 part by weight of a compound I is dissolved in a mixture     which consists of 70 parts by height of cyclohexanone, 20 parts by     weight of ethoxylated isooctylphenol and 10 parts by weight of     ethoxylated castor oil. A stable emulsion concentrate is obtained. -   VIII. 1 part by weight of a compound I is dissolved in a mixture     which consists of 80 parts by weight of cyclohexanone and 20 parts     by weight of Wettol® EM31 (=nonionic emulsifier based on ethoxylated     castor oil; BASF AG). A stable emulsion concentrate is obtained.

The active compounds I or the herbicidal compositions can be applied by the preemergence or postemergence method. The herbicidal compositions or active compounds can also be applied by sowing crop seed which has been pretreated with the herbicidal compositions or active compounds. If the active ingredients are less well tolerated by certain crops, it is possible to use application methods in which the herbicidal compositions are sprayed with the aid of the sprayers in such a way that the leaves of the sensitive crops are as far as possible not affected, while the active compounds reach the leaves of undesirable plants growing underneath or the uncovered soil surface (post-directed, lay-by).

The application rates of active compound I are from 0.001 to 3.0, preferably from 0.01 to 1.0, kg/ha of active ingredient (a.i.), depending on the aim of control, the season, the target plants and the state of growth.

In order to broaden the action spectrum and to achieve synergistic effects, the compounds I according to the invention may be mixed with many members of other groups of herbicidal or growth-regulating active ingredients and applied together with them.

Examples of suitable components of the mixture are 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and derivatives thereof, aminotriazoles, anilides, aryloxy-/hetaryloxyalkanoic acids and derivatives thereof, benzoic acid and derivatives thereof, benzothiadiazinones, 2-(hetaroyl/aroyl)-1,3-cyclohexanediones, hetarylarylketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates, quinolinecarboxylic acid and derivatives thereof, chloroacetanilides, cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid and derivatives thereof, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and derivatives thereof, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryloxyphenoxypropionic esters, phenylacetic acid and derivatives thereof, 2-phenylpropionic acid and derivatives thereof, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and derivatives thereof, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolcarboxamides and uracils.

It may also be useful to apply the compounds I together, alone or in combination with other herbicides, also as a mixture with further crop-protection agents, for example with pesticides or agents for controlling phytopathogenic fungi or bacteria. The miscibility with mineral salt solutions which are used for eliminating nutrient and trace element deficiencies is also of interest. Nonphytotoxic oils and oil concentrates can also be added.

The examples below are intended to illustrate the invention without limiting it.

PREPARATION EXAMPLES

The products were characterized by HPLC/MS (high performance liquid chromatography/mass spectrometry), by ¹H-NMR spectroscopy or by their melting point.

HPLC column: RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany).

Mobile phase: acetonitrile +0.1% trifluoroacetic acid (TFA)/water +0.1% TFA in a gradient from 5:95 to 95:5 over 5 minutes, at 40° C.

MS: quadrupole electrospray ionization, 80 V (positive mode)

Example 1 1-(3-trifluoromethyl)phenyl-3-(N-methyl)carboxamido-2-pyrrolidinone

1.1: 1-(3-trifluoromethyl)phenyl-2-pyrrolidinone

54 g (0.34 mol) of 3-trifluoromethylaniline, 110 ml of butyrolactone and 5 ml of concentrated hydrochloric acid were heated at reflux for 13 hours. Excess butyrolactone was then removed under reduced pressure. The resulting crystalline residue was washed initially with an aqueous sodium bicarbonate solution and then with water and subsequently with pentane. Drying gave 65.5 g (85% of theory) of 1-(3-trifluoromethyl)phenyl-2-pyrrolidinone.

¹H-NMR (270 MHz, CDCl₃) δ (ppm): 7.85 (m, 2H), 7.45 (t, 1H), 7.4 (d, 1H), 3.85 (t, 2H), 2.6 (t, 2H), 2.2 (qu, 2H).

1.2: 2-oxo-1-(3-trifluoromethyl)phenyl-3-pyrrolidinecarboxylic acid

Under nitrogen, 50 ml of absolute tetrahydrofuran were added to 13.6 g (0.06 mol) of 1-(3-trifluoromethyl)phenyl-2-pyrrolidinone from 1.1, the mixture was cooled to 0° C. and 60 ml of 2M (0.12 mol) lithium diisoproylamide in a solvent mixture of heptane, tetrahydrofuran and ethylbenzene were added. The reaction mixture was stirred at 0° C. for 45 minutes. 5.4 g (0.06 mol) of dimethyl carbonate in 10 ml of absolute tetrahydrofuran were then added. After the addition had ended, the reaction mixture was allowed to warm to 20° C. and stirred for another 72 hours. The solvent was evaporated under reduced pressure and methyl tert-butyl ether and water were then added to the resulting residue, the phases were separated and the organic phase was extracted twice with water. The aqueous phase was acidified with hydrochloric acid (10% by weight) to pH=1. The mixture was extracted twice with in each case 100 ml of ethyl acetate and the combined organic phase was dried and concentrated under reduced pressure. This gave 5.61 g (34% of theory) of 2-oxo-1-(3-trifluoromethyl)phenyl-3-pyrrolidinecarboxylic acid of melting point 121° C.

¹H-NMR (400 MHz, CDCl₃) δ (ppm): 7.9 (s, 1H), 7.8 (d, 1H), 7.5 (t, 1H), 7.45 (d, 1H), 4.1-3.9 (m, 2H), 3.7 (t, 1H), 2.55 (m, 2H).

1.3: 1-(3-trifluoromethyl)phenyl-3-(N-methyl)carboxamido-2-pyrrolidinone

0.14 g (1.8 mmol) of a 40% strength aqueous methylamine solution was added to 0.5 g (1.8 mmol) of 2-oxo-1-(3-trifluoromethyl) phenyl-3-pyrrolidinecarboxylic acid from 1.2 in 50 ml of dichloromethane and 0.35 g (2 mmol) of 1,1′-carbonyldiimidazole. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was extracted with saturated aqueous ammonium chloride solution and the organic phase was then extracted with water. The organic phase was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure and the residue that remained was then titrated with methyl tert-butyl ether. The insoluble fraction was then separated off, and the residue was washed with methyl tert-butyl ether. This gave 0.166 g (32% of theory) of the title compound of melting point 128° C.

¹H-NMR (400 MHz, CDCl₃) δ (ppm): 7.9 (s, 1H), 7.75 (d, 1H), 7.5 (t, 1H), 7.4 (d, 1H), 7.3-7.2 (br, 1H), 4.0-3.8 (m, 2H), 3.5 (t, 1H), 2.9 (d, 3H), 2.75-2.6 (m, 1H), 2.55-2.45 (m, 1H).

Example 2 1-(3-trifluoromethoxy)phenyl-3-acetyloxy-3-(N-phenyl)carboxamido-2-pyrrolidinone

0.34 g (0.93 mmol) of 1-(3-trifluoromethoxy)phenyl-3-(N-phenyl)-carboxamido-2-pyrrolidinone, prepared analogously to Example 1 using the starting material 3-trifluoromethoxyaniline, was initially charged in 3 ml of dry dimethylformamide (DMF), and 0.04 g (0.093 mmol) of sodium hydride (60% in mineral oil) was added at 20° C. The mixture was then stirred at 20° C. for 30 min, 0.07 g (0.093 mmol) of acetyl chloride was then added and the mixture was stirred at 20° C. for another 18 h. Water was added and the mixture was extracted repeatedly with dichloromethane. The combined organic phases were washed with water, the solvent was removed and the residue was chromatographed. This gave 0.27 g of the title compound of melting point 140° C.

The compounds of Examples 3 to 191 were prepared in an analogous manner: TABLE 2

m.p. [° C.] or RT Example (A)_(n) R* R¹ R² R³ (HPLC/MS) 1 — 3-CF₃ H methyl H 128 2 — 3-OCF₃ OC(O)CH₃ phenyl H 140 3 — 3-CF₃ H ethyl H 122 4 — 3-CF₃ H n-propyl H 112 5 — 3-CF₃ H n-butyl H 111 6 — 3-CF₃ H tert-butyl H oil 7 — 3-CF₃ H cyclopentyl H oil 8 — 3-CF₃ H ethyl ethyl oil 9 — 3-CF₃ H methyl n-butyl oil 10 — 3-CF₃ H phenyl H oil 11 — 3-CF₃ H CH(CH₃)₂ H 136 12 — 3-CF₃ H cyclohexyl H 141 13 — 3-CF₃ H CH₂-cyclopropyl H 108 14 — 3-CF₃ H cyclopropyl H oil 15 — 3-CF₃ H methyl methyl oil 16 — 3-CF₃ H cyclopropyl methyl oil 17 O 3-CF₃ H t-butyl H 122 18 — 3-OCF₃ H methyl H 103 19 — 3-OCF₃ H ethyl H 111 20 — 3-OCF₃ H n-propyl H 110 21 — 3-OCF₃ H tert-butyl H  89 22 — 3-OCF₃ H cyclopentyl H 140 23 — 3-OCF₃ H methyl n-butyl oil 24 — 3-OCF₃ H phenyl H 108 25 — 3-OCF₃ H CH(CH₃)₂ H 134 26 — 3-OCF₃ H cyclopropyl H 134 27 — 3-OCF₃ H methyl methyl oil 28 — 3-OCF₃ H H H 106 29 O 3-OCF₃ H H H 124 30 — 3-OCF₃ OC(O)CH₃ cyclopentyl H oil 31 O 3-OCF₃ H methyl H  98 32 — 3-OCF₃ CH₃ tert-butyl H  40 33 O 3-OCF₃ H CH₂-phenyl H 108 34 O 3-OCF₃ H methyl methyl oil 35 O 3-OCF₃ H CH(CH₃)₂ H 123 36 O 3-OCF₃ H CH₂CH═CH₂ H  75 37 O 3-OCF₃ H CH₂C(Cl)═CH₂ H  68 38 O 3-OCF₃ H CH₂CH₂CH₂  29 39 O 3-OCF₃ H CH₂CH═CHCH₃ H  87 40 O 3-OCF₃ H CH₂CH═CHCl H  62 41 O 3-OCF₃ H CH₂CH₃ H 100 42 O 3-OCF₃ H CH₂CH₂OCH₃ H  85 43 O 3-OCF₃ H cylohexyl H 152 44 O 3-OCF₃ H CH₂-cylohexyl H 135 45 — 3-CH(CH₃)₂ H tert-butyl H  51 46 — 3-CH(CH₃)₂ CH₃ tert-butyl H  78 47 O 3-CF₃ H tert-butyl H oil 48 O 3-OCF₃ H tert-butyl H 112 49 — 2-Cl H tert-butyl H  76 50 — 3-Cl H tert-butyl H 118 51 — 3-Cl; 5-Cl H tert-butyl H 130 52 — 2-Cl; 4-Cl H tert-butyl H  93 53 — 2-F H tert-butyl H 113 54 — 2-CF₃ H tert-butyl H  90 55 — 4-CF₃ H tert-butyl H 155 56 — 2-CH₃ H tert-butyl H  93 57 — 3-CH₃ H tert-butyl H  88 58 — 4-CH₃ H tert-butyl H 135 59 — 2-CH(CH₃)₂ H tert-butyl H 104 60 — 3-OCH₃ H tert-butyl H  43 61 — 4-OCH₃ H tert-butyl H 132 62 — 2-OCH₃ H tert-butyl H oil 63 — 2-Cl; 6-Cl H tert-butyl H oil 64 — 2-Cl; 3-Cl H tert-butyl H oil 65 — 4-Cl H tert-butyl H 155 66 — 3-OCH₃ H

H 110-112 67 — 3-OCF₃ H

H 3.78 min, m/z = 405 [M + H]⁺ 68 — 3-OCF₃ H

H 4.09 min, m/z = 399 [M + H]⁺ 69 — 3-OCF₃ H

H 3.62 min, m/z = 391 [M + H]⁺ 70 — 3-OCF₃ H

H 3.89 min, m/z = 397 [M + H]⁺ 71 — 3-OCF₃ H

H 4.30 min, m/z = 469 [M + H]⁺ 72 — 3-OCF₃ H

H 4.03 min, m/z = 469 [M + H]⁺ 73 — 3-OCF₃ H

H 3.95 min, m/z = 443 [M + Na]⁺ 74 — 3-OCF₃ H

H 3.93 min, m/z = 443 [M + Na]⁺ 75 — 3-OCF₃ H

H 3.61 min, m/z = 525 [M + H]⁺ 76 — 3-OCF₃ H

H 3.75 min, m/z = 459 [M + Na]⁺ 77 — 3-OCF₃ H

H 3.55 min, m/z = 489 [M + Na]⁺ 78 — 3-OCF₃ H

H 3.84 min, m/z = 373 [M + H]⁺ 79 — 3-OCF₃ H

H 4.11 min, m/z = 498 [M + Na]⁺ 80 — 3-OCF₃ H

H 3.79 min, m/z = 443 [M + H]⁺ 81 — 3-OCF₃ H

H 3.88 min, m/z = 373 [M + H]⁺ 82 — 3-OCF₃ H

H 3.60 min, m/z = 387 [M + H]⁺ 83 — 3-OCF₃ H

H 3.80 min, m/z = 429 [M + Na]⁺ 84 — 3-OCF₃ H

H 3.37 min, m/z = 355 [M + H]⁺ 85 — 3-OCF₃ H

H 3.17 min, m/z = 356 [M + H]⁺ 86 — 3-OCF₃ H

H 4.20 min, m/z = 401 [M + H]⁺ 87 — 3-OCF₃ H

H 3.33 min, m/z = 405 [M + H]⁺ 88 — 3-OCF₃ H

H 3.52 min, m/z = 435 [M + H]⁺ 89 — 3-OCF₃ H

H 3.91 min, m/z = 451 [M + H]⁺ 90 — 3-OCF₃ H

H 4.20 min, m/z = 491 [M + Na]⁺ 91 — 3-OCF₃ H

H 3.18 min, m/z = 389 [M + H]⁺ 92 — 3-OCF₃ H

H 3.85 min, m/z = 460 [M + Na]⁺ 93 — 3-OCF₃ H

H 4.03 min, m/z = 475 [M + H]⁺ 94 — 3-OCF₃ H

H 3.82 min, m/z = 579 [M + Na]⁺ 95 — 3-OCF₃ H

H 3.19 min, m/z = 401 [M + H]⁺ 96 — 3-OCF₃ H

H 3.32 min, m/z = 481 [M + H]⁺ 97 — 3-OCF₃ H

H 3.75 min, m/z = 383 [M + H]⁺ 98 — 3-OCF₃ H

H 4.26 min, m/z = 401 [M + H]⁺ 99 — 3-OCF₃ H

H 4.06 min, m/z = 411 [M + H]⁺ 100 — 3-OCF₃ H

H 3.54 min, m/z = 415 [M + H]⁺ 101 — 3-OCF₃ H

H 3.79 min, m/z = 429 [M + H]⁺ 102 — 3-OCF₃ H

H 3.77 min, m/z = 429 [M + H]⁺ 103 — 3-OCF₃ H

H 4.09 min, m/z = 435 [M + H]⁺ 104 — 3-OCF₃ H

H 3.98 min, m/z = 439 [M + H]⁺ 105 — 3-OCF₃ H

H 3.75 min, m/z = 383 [M + H]⁺ 106 — 3-OCF₃ H

H 2.93 min, m/z = 421 [M + H]⁺ 107 — 3-OCF₃ H

H 3.63 min, m/z = 504 [M + H]⁺ 108 — 3-OCHF₂ H phenyl H 104 109 — 3-OCHF₂ H

H  80 110 — 3-OCHF₂ H tert-butyl H  64 111 — 3-OCHF₂ H

H oil 112 — 3-OCHF₂ H

H 153 113 — 3-OCHF₂ H

H oil 114 — 3-OCHF₂ H

H oil 115 — 3-OCHF₂ H

H  48 116 — 3-OCHF₂ H

H oil 117 — 3-OCHF₂ H

H  82 118 — 3-OCHF₂ H

H oil 119 — 3-OCHF₂ H CH₃ H  74 120 — 3-OCHF₂ H ethyl H  70 121 — 3-OCHF₂ H isopropyl H 126 122 — 3-OCHF₂ H cylopropyl H 130 123 — 4-CH═C(Cl)₂ H tert-butyl H 166-167 124 — 3-CF₃; H tert-butyl H 135-136 5-CF₃ 125 — 4-SCH₃ H tert-butyl H 166-167 126 — 4-CH(CH₃)₂ H tert-butyl H 130-131 127 — 4-OCHF₂ H tert-butyl H 152-153 128 — 3-Cl; H tert-butyl H 160-163 4-Cl; 5-Cl 129 — 3-Br; H tert-butyl H 140-141 5-Br 130 — 4-NO₂; H tert-butyl H 152-153 5-Cl 131 — 4-OCF₂CF₃ H tert-butyl H 66-67 132 — 3-OCF₃ H

H oil 133 — 3-OCF₃ H

H 3.51 min, m/z = 357 [M + H]⁺ 134 — 3-OCF₃ H

H 3.67 min, m/z = 359 [M + H]⁺ 135 — 3-OCF₃ H

H 2.92 min, m/z = 361 [M + H]⁺ 136 — 3-OCF₃ H

H 3.31 min, m/z = 370 [M + H]⁺ 137 — 3-OCF₃ H

H 3.23 min, m/z = 370 [M + H]⁺ 138 — 3-CF₃; H tert-butyl H 3.65 min 4-Cl m/z = 363 [M + H]⁺ 139 — 3-OCH₃; H tert-butyl H 2.87 min 5-OCH₃ m/z = 321 [M + H]⁺ 140 — 3-SCH₃ H tert-butyl H 3.14 min m/z = 307 [M + H]⁺ 141 — 3-tert- H tert-butyl H 3.62 min butyl m/z = 317 [M + H]⁺ 142 — O—CH(CH₃)₂ H tert-butyl H 3.24 min m/z = 319 [M + H]⁺ 143 — 3-F; H tert-butyl H 3.07 min 4-F m/z = 297 [M + H]⁺ 144 — 3-OCH₃; H tert-butyl H 3.65 min 4-OCH₃; m/z = 351 5-OCH₃ [M + H]⁺ 145 — 4-propyl H tert-butyl H 3.53 min m/z = 303 [M + H]⁺ 146 — 4-O-tert- H tert-butyl H 3.36 min butyl m/z = 333 [M + H]⁺ 147 — 3-Cl; H tert-butyl H 3.26 min 4-F m/z = 313 [M + H]⁺ 148 — 4-O-propyl H tert-butyl H 3.67 min m/z = 319 [M + H]⁺ 149 — 4-Br H tert-butyl H 3.19 min m/z = 339 [M + H]⁺ 150 — 4-SCH₂CH₃ H tert-butyl H 3.32 min m/z = 321 [M + H]⁺ 151 — 3-Br; H tert-butyl H 3.49 min 4-OCH₃; m/z = 405 5-Cl [M + H]⁺ 152 — 3-Cl; H tert-butyl H 3.58 min 4-O-propyl m/z = 353 [M + H]⁺ 153 — 3-F; H tert-butyl H 2.97 min 4-NO₂ m/z = 324 [M + H]⁺ 154 — 3-Br; H tert-butyl H 3.86 min 5-Br; m/z = 452 4-Cl [M + H]⁺ 155 — 3-ethyl; H tert-butyl H 3.47 min 5-CH₃ m/z = 303 [M]⁺ 156 — 3-CH₂; H tert-butyl H 3.22 min 5-CH₃ m/z = 289 [M + H]⁺ 157 — 3-Br H tert-butyl H 3.21 min m/z = 341 [M + H]⁺ 158 — 3-ethyl H tert-butyl H 3.23 min m/z = 289 [M + H]⁺ 159 — 3-iso- H tert-butyl H 3.46 min propyl; m/z = 333 4-OCH₃ [M + H]⁺ 160 — 3,4- H tert-butyl H 2.66 min OCH₂CH₂O— m/z = 319 [M + H]⁺ 161 — 4-CN H tert-butyl H 2.74 min m/z = 286 [M + H]⁺ 162 — 3-CN; H tert-butyl H 2.74 min 4-OCH₃ m/z = 316 [M + H]⁺ 163 — 3-CN; H tert-butyl H 2.79 min 4-F m/z = 304 [M + H]⁺ 164 — 3-F; H tert-butyl H 3.22 min 4-CH₃ m/z = 293 [M + H]⁺ 165 — 3-CN; H tert-butyl H 3.09 min 4-Cl m/z = 320 [M + H]⁺ 166 — 3-Cl; H tert-butyl H 3.53 min 4-Cl m/z = 329 [M]⁺ 167 — 3-CH₃; H tert-butyl H 3.11 min 4-F m/z = 293 [M + H]⁺ 168 — 3-Cl; H tert-butyl H 3.06 min 4-OCH₃ m/z = 325 [M + H]⁺ 169 — 4-heptyl H tert-butyl H 4.50 min m/z = 359 [M + H]⁺ 170 — 4-tert- H tert-butyl H 3.73 min butyl m/z = 317 [M + H]⁺ 171 — 4-ethyl H tert-butyl H 3.32 min m/z = 289 [M + H]⁺ 172 — 3-Cl; H tert-butyl H 3.82 min 4-iso- m/z = 337 propyl [M + H]⁺ 173 — 3-Cl; H tert-butyl H 3.45 min 4-CH₃ m/z = 309 [M]⁺ 174 — 3-F H tert-butyl H 3.96 min m/z = 279 [M + H]⁺ 175 — 3-CH₃; H tert-butyl H 94-96 5-propyl 176 — 3-ethyl; H tert-butyl H 120-122 5-ethyl 177 — 3-O-ethyl H tert-butyl H 86-88 178 — 3-OCH₃; H tert-butyl H 150-152 4-Br 179 — 3-OCH₃; H tert-butyl H 137-139 4-Cl 180 — 3-Cl; H tert-butyl H 3.86 min 4-SCF₃ m/z = 395 [M + H]⁺ 181 — 4-F H tert-butyl H 2.77 min m/z = 278 [M + H]⁺ 182 — 3-OCF₃ H

H 4.16 min m/z = 423 [M + H]⁺ 183 — 3-OCF₃ H

H 4.31 min m/z = 469 [M + H]⁺ 184 — 3-OCF₃ H

H 3.87 min m/z = 443 [M + H]⁺ 185 — 3-OCF₃ H

H 3.76 min m/z = 447 [M + Na]⁺ 186 — 3-OCF₃ H

H 3.00 min m/z = 402 [M + H]⁺ 187 — 3-OCF₃ H

H 3.75 min m/z = 453 [M + Na]⁺ 188 — 3-OCF₃ H

H 3.94 min m/z = 463 [M + Na]⁺ 189 — 3-OCF₃ H

H 4.42 min m/z = 553 [M + Na]⁺ 190 — 3-OCF₃ H

H 3.85 min m/z = 473 [M + Na]⁺ 191 — 3-OCF₃ H

H 4.49 min m/z = 611 [M + Na]⁺ *The number in front of the substituent denotes the position of the substituent on the phenyl ring. ● Attachment site RT = retention time, HPLC/MS m.p. = melting point phenyl = C₆H₅

Example 192 1-(3-trifluoromethoxy)phenyl-3-(N-(1,1-dimethylethyl))carboxamido-2-pyrrolidinethione and 1-(3-trifluoromethoxy)phenyl-3-(N-(1,1-dimethylethyl))thiocarboxamido-2-pyrrolidinone

0.26 g (0.7 mmol) of 1-(3-trifluoromethoxy)phenyl-3-(N-(1,1-di-methylethyl))carboxamido-2-pyrrolidinone was initially charged in 3 ml of dry toluene, and 0.17 g (0.42 mmol) of 2,4-bis(4-methoxy-phenyl)-1,3-dithia-2,4-diphosphetane-2,4-dithione (Lawesson's reagent) was added at 20° C., and the mixture was heated at 70° C. for 7 h. The reaction mixture was then washed twice with water. The solvent was removed and the residue was chromatographed on silica gel using a mixture of cyclohexane/ethyl acetate as mobile phase. A first fraction gave 0.06 g (22%) of 1-(3-trifluoromethoxy)phenyl-3-(N-(1,1-dimethyl-ethyl))thiocarboxamido-2-pyrrolidinone of melting point 65° C. and 0.08 g (29%) of 1-(3-trifluoromethoxy)phenyl-3-(N-(1,1-dimethyl-ethyl))carboxamido-2-pyrrolidinethione of melting point 116° C.

Use Examples

The herbicidal activity of the 1-phenylpyrrolidon-2-one-3-carboxamides of the formula I was demonstrated by the following greenhouse experiments:

The cultivation containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

For the preemergence treatment, directly after sowing the active compounds, which had been suspended or emulsified in water, were applied by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover causes uniform germination of the test plants, unless this was adversely affected by the active compounds.

For the postemergence treatment, the test plants were first grown to a height of 3-15 cm, depending on the plant habit, and only then treated with the active compounds which had been suspended or emulsified in water. The test plants were for this purpose either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to the treatment. The application rate for the pre- and postemergence treatment was 3.0 kg of a.i./ha.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the above-ground parts, and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments were of the following species: Bayer code Common name ABUTH Velvetleaf AVEFA wild Oat LOLMU italien Ryegrass SETIT Millet SINAL velvetleaf

At application rates of 3 kg/ha, the compound from Example 3, applied by the post-emergence method, shows very good herbicidal activity against AVEFA and SINAL.

At application rates of 3 kg/ha, the compound from Example 18, applied by the post-emergence method, shows very good herbicidal activity against ABUTH, SETIT and SINAL.

At application rates of 3 kg/ha, the compound from Example 18, applied by the pre-emergence method, shows very good herbicidal activity against ABUTH, SETIT and SINAL.

At application rates of 3 kg/ha, the compound from Example 19, applied by the pre-emergence method, shows very good herbicidal activity against ABUTH and SINAL.

At application rates of 3 kg/ha, the compound from Example 26, applied by the post-emergence method, shows very good herbicidal activity against AVEFA and SINAL.

At application rates of 3 kg/ha, the compound from Example 26, applied by the pre-emergence method, shows very good herbicidal activity against ABUTH, LOLMU and SINAL. 

1. A compound which is a 1-phenylpyrrolidin-2-one-3-carboxamide of the formula I

where the variables R¹, R², R³, X, Y, A, n, R^(a), R^(b), R^(c), R^(d) and R^(e) are as defined below: R¹ is hydrogen, OH, Cl, Br, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C(O)R⁴ or OC(O)R⁴; R² and R³ independently of one another are hydrogen, C₁-C₁₀-alkyl, C₃-C₁₀-cycloalkyl, C₇-C₁₀-polycycloalkyl, C₃-C₈-alkenyl, C₃-C₁₀-alkynyl, C₅-C₁₀-cycloalkenyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, phenyl or 3- to 7-membered heterocyclyl, where the 9 last-mentioned groups may be unsubstituted, partially or fully halogenated and/or substituted by 1, 2 or 3 radicals selected from the group consisting of OH, CN, NO₂, COOH, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkylthio, C₁-C₄-haloalkylthio, unsubstituted or substituted phenyl, COOR⁵, NR⁶R⁷, C(O)NR⁸SO2R¹³, C(O)NR⁸R⁹ and 3- to 7-membered heterocyclyl, wherein each heterocyclyl may contain 1, 2 or 3 heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur, a group NR¹⁰ and a group SO₂, and, if appropriate, 1, 2 or 3 carbonyl groups and/or thiocarbonyl groups as ring members; and/or may contain a ring-fused phenyl ring which is unsubstituted or substituted; or R² and R³, together with the group N-(A)_(n) to which they are attached, form a saturated 3- to 7-membered heterocycle which, in addition to the nitrogen atom, may contain 1, 2 or a further 3 heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur and a group NR¹⁰ and, if appropriate, 1, 2 or 3 carbonyl groups and/or thiocarbonyl groups as ring members; R^(a), R^(b), R^(c), R^(d) and R^(e) independently of one another are hydrogen, OH, CN, NO₂, halogen, C₁-C₁₀-alkyl, C₃-C₆-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkylthio, C₁-C₄-haloalkylthio, C(O)R⁴, COOR⁵, NR⁶R⁷, C(O)NR⁸R⁹, S(O)₂NR⁸R⁹, S(O)R¹¹, S(O)₂R¹¹ or C₁-C₄-alkoxy-C₁-C₆-alkyl; or two adjacent radicals R^(a) to R^(e), together with the atoms to which they are attached, form a 5-, 6- or 7-membered saturated or unsaturated ring which may contain one or two heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur and a group NR¹⁰ as ring-forming atom and/or may carry one, two, three or four radicals selected from the group consisting of halogen and C₁-C₄-alkyl; X, Y independently of one another are oxygen or sulfur; n is 0 or 1; A is O, S(O)_(k) or NR¹², where k is 0, 1 or 2; R⁴, R⁸, R⁹ independently of one another are hydrogen or C₁-C₄-alkyl; R⁵, R¹¹ are C₁-C₄-alkyl; R⁶, R⁷ independently of one another are hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C(O)R⁴, COOR⁵ or S(O)₂R¹¹; R¹⁰, R¹² independently of one another are hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl; and R¹³ is phenyl which is unsubstituted or carries 1, 2, 3 or 4 substituents, where the substituents are selected from the group consisting of halogen, nitro, cyano, OH, alkyl, alkoxy, haloalkyl, haloalkoxy, COOR⁵, NR⁶R⁷ and C(O)NR⁸R⁹; or an agriculturally useful salt thereof.
 2. A compound as claimed in claim 1 in which R² and R³ independently of one another are hydrogen, C₁-C₁₀-alkyl, C₃-C₁₀-cycloalkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl, C₅-C₁₀-cycloalkenyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, phenyl or 3- to 7-membered heterocyclyl, where the 8 last-mentioned groups may be unsubstituted, partially or fully halogenated and/or substituted by 1, 2 or 3 radicals selected from the group consisting of OH, CN, NO₂, COOH, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkylthio, C₁-C₄-haloalkylthio, unsubstituted or substituted phenyl, COOR⁵, NR⁶R⁷, C(O)NR R⁹, wherein each heterocyclyl may contain 1, 2 or 3 heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur and a group NR¹⁰ and, if appropriate, 1, 2 or 3 carbonyl groups and/or thiocarbonyl groups as ring members; or R² and R³, together with the group N-(A)_(n) to which they are attached, form a saturated 3- to 7-membered heterocycle which, in addition to the nitrogen atom, may contain 1, 2 or a further 3 heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur and a group NR¹⁰ and, if appropriate, 1, 2 or 3 carbonyl groups and/or thiocarbonyl groups as ring members.
 3. A compound as claimed in claim 1 wherein R¹ is hydrogen.
 4. A compound as claimed in claim 1 wherein R³ is hydrogen or C₁-C₄-alkyl.
 5. A compound as claimed in claim 1 wherein R² is C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₅-C₆-cycloalkenyl, substituted or unsubstituted phenyl, C₃-C₆-cycloalkyl-C₁-₄-alkyl, where C₁-C₆-alkyl and C₃-C₆ cycloalkyl may be partially or fully halogenated and/or may contain a at least one radical selected from the group consisting of C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkylthio, C₁-C₄-haloalkylthio, unsubstituted or substituted phenyl, COOR⁵, NR⁶R⁷ and C(O)NR⁸R⁹.
 6. A compound as claimed in claim 1 wherein X and Y represent oxygen.
 7. A compound as claimed in claim 1 wherein n=0.
 8. A compound as claimed in claim 1 wherein the radicals R^(a), R^(b), R^(c), R^(d) and R^(e) are selected from the group consisting of hydrogen, halogen, CN, C₁-C₄-alkyl, OCH₃, CF₃, CHF₂, OCF₃ and OCHF₂.
 9. A compound as claimed in claim 1 wherein not more than 3 of the radicals R^(a), R^(b), R^(c), R^(d) and R^(e) are different from hydrogen.
 10. A compound as claimed in claim 1 wherein 2 or 3 of the radicals R^(a), R^(b), R^(c), R^(d) and R^(e) are different from hydrogen.
 11. A compound as claimed in claim 9 wherein the radicals R^(a) and R^(e) represent hydrogen.
 12. A composition, comprising a herbicidally effective amount of at least compound as claimed in claim 1, and at least one inert liquid and/or solid carrier, and, if desired, at least one surfactant.
 13. A method for controlling unwanted vegetation, which comprises allowing a herbicidally effective amount of at least one compound as claimed in claim 1 to act on plants, their habitat or on seed.
 14. A method for controlling unwanted vegetation, comprising applying to plants, their habitat or to their seed a herbicidally effective amount of at least one compound of claim
 1. 15. The method of claim 14, wherein said compound is applied at an application rate of from 0.001 to 3.0 kg/ha.
 16. The method of claim 15, wherein the application rate of said compound is 0.01 to 1.0 kg/ha.
 17. A compound of claim 1, wherein n is 1 and A, is oxygen, a group N—R¹², where R¹²=hydrogen or alkyl, or a group SO₂.
 18. A compound of claim 1, wherein R^(a), R^(b), R^(c), R^(d), R^(e) are independently hydrogen, halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.
 19. A compound of claim 1, wherein R¹ is hydrogen, OH, Cl, Br, C₁-C₆-alkyl or OC(O)R⁴.
 20. A compound of claim 1, wherein R² is C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl, C₃-C₈-cycloalkyl, C₅-C₈-cycloalkenyl or C₃-C₈-cycloalkyl-C₁-C₄-alkyl, where C¹-C₁₀-alkyl and C₃-C₈-cycloalkyl may be partially or fully halogenated and/or may carry one or two radicals selected from the group consisting of C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkylthio, C¹-C₄-haloalkylthio, unsubstituted or substituted phenyl, COOR⁵, NR⁶R⁷, C(O)NR⁸R⁹, phenyl which may be unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of halogen, nitro, OH, CN, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkylthio, C₁-C₄-haloalkylthio, unsubstited or substituted phenyl, COOR⁵, NR⁶R⁷ and C(O)NR⁸R⁹.
 21. A compound of formula (Ia)

wherein R^(b), R^(c), R^(d) independently of one another are hydrogen, OH, CN, NO₂, halogen, C₁-C₁₀-alkyl, C₃-C₆-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkylthio, C₁-C₄-haloalkylthio, C(O)R⁴, COOR⁵, NR⁶R⁷, C(O)NR⁸R⁹, S(O)₂NR⁸R⁹, S(O)R¹¹, S(O)₂R¹¹ or C₁-C₄-alkoxy-C₁-C₆-alkyl; and R² is hydrogen, C₁-C₁₀-alkyl, C₃-C₁₀-cycloalkyl, C₇-C₁₀-polycycloalkyl, C₃-C₈-alkenyl, C₃-C₁₀-alkynyl, C₅-C₁₀-cycloalkenyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, phenyl or 3- to 7-membered heterocyclyl, where the 9 last-mentioned groups may be unsubstituted, partially or fully halogenated and/or contain 1, 2 or 3 radicals selected from the group consisting of OH, CN NO₂, COOH, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₂-C₆-alkenyl, C₂-C₆ alkynyl, C₁-C₆-alkylthio, C₁-C₄-haloalkylthio, unsubstituted or substituted phenyl, COOR⁵, NR⁶R⁷, C(O)NR⁸SO₂R¹³, C(O)NR⁸R⁹ and 3- to 7-membered heterocyclyl, wherein each hetercyclyl may contain 1, 2 or 3 heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur, a group NR¹⁰ and a group SO₂, and, if appropriate, 1, 2 or 3 carbonyl groups and/or thiocarbonyl groups as ring members; and/or may contain a ring-fused phenyl ring which is unsubstituted or substituted. 